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Origins of the double asymmetric induction on proline-catalyzed aldol reactions
被引:38
作者
:
Calderon, Felix
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Calderon, Felix
[
1
]
Doyagueez, Elisa G.
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Doyagueez, Elisa G.
[
1
]
Cheong, Paul Ha-Yeon
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Cheong, Paul Ha-Yeon
[
2
]
Fernandez-Mayoralas, Alfonso
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Fernandez-Mayoralas, Alfonso
[
1
]
Houk, K. N.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Houk, K. N.
[
2
]
机构
:
[1]
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
[2]
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
2008年
/ 73卷
/ 20期
关键词
:
D O I
:
10.1021/jo800934b
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
Computational studies to elucidate the origin of the double asymmetric induction on proline-catalyzed aldol reaction have been performed using HF/6-31G(d) calculations. The computed transition structures explain the experimental data obtained.
引用
收藏
页码:7916 / 7920
页数:5
相关论文
共 23 条
[1]
Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions
[J].
Allemann, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Allemann, C
;
Gordillo, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Gordillo, R
;
Clemente, FR
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Clemente, FR
;
Cheong, PHY
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Cheong, PHY
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(08)
:558
-569
[2]
Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
[J].
Bahmanyar, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Bahmanyar, S
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
;
Martin, HJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Martin, HJ
;
List, B
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
List, B
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(09)
:2475
-2479
[3]
The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions
[J].
Bahmanyar, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Bahmanyar, S
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(51)
:12911
-12912
[4]
Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity
[J].
Bahmanyar, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Bahmanyar, S
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(45)
:11273
-11283
[5]
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6]
A proline-catalyzed asymmetric Robinson annulation reaction
[J].
Bui, T
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Bui, T
;
Barbas, CF
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Barbas, CF
.
TETRAHEDRON LETTERS,
2000,
41
(36)
:6951
-6954
[7]
Asymmetric aldol reaction using immobilized proline on mesoporous support
[J].
Calderón, F
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Calderón, F
;
Fernández, R
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Fernández, R
;
Sánchez, F
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Sánchez, F
;
Fernández-Mayoralas, A
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Fernández-Mayoralas, A
.
ADVANCED SYNTHESIS & CATALYSIS,
2005,
347
(10)
:1395
-1403
[8]
Synthesis of azasugars through a proline-catalyzed reaction
[J].
Calderon, Felix
论文数:
0
引用数:
0
h-index:
0
机构:
Instituto de Química Orgánica General, C/Juan de la Cierva
Calderon, Felix
;
Doyaguez, Elisa G.
论文数:
0
引用数:
0
h-index:
0
机构:
Instituto de Química Orgánica General, C/Juan de la Cierva
Doyaguez, Elisa G.
;
Fernandez-Mayoralas, Alfonso
论文数:
0
引用数:
0
h-index:
0
机构:
Instituto de Química Orgánica General, C/Juan de la Cierva
Fernandez-Mayoralas, Alfonso
.
JOURNAL OF ORGANIC CHEMISTRY,
2006,
71
(16)
:6258
-6261
[9]
Pipecolic acid-catalyzed direct asymmetric Mannich reactions
[J].
Cheong, PHY
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Cheong, PHY
;
Zhang, HL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Zhang, HL
;
Thayumanavan, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Thayumanavan, R
;
Tanaka, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Tanaka, F
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
;
Barbas, CF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Barbas, CF
.
ORGANIC LETTERS,
2006,
8
(05)
:811
-814
[10]
Computational evidence for the enamine mechanism of intramolecular Aldol reactions catalyzed by proline
[J].
Clemente, FR
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Clemente, FR
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004,
43
(43)
:5766
-5768
←
1
2
3
→
共 23 条
[1]
Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions
[J].
Allemann, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Allemann, C
;
Gordillo, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Gordillo, R
;
Clemente, FR
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Clemente, FR
;
Cheong, PHY
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Cheong, PHY
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(08)
:558
-569
[2]
Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
[J].
Bahmanyar, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Bahmanyar, S
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
;
Martin, HJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Martin, HJ
;
List, B
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
List, B
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(09)
:2475
-2479
[3]
The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions
[J].
Bahmanyar, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Bahmanyar, S
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(51)
:12911
-12912
[4]
Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity
[J].
Bahmanyar, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Bahmanyar, S
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(45)
:11273
-11283
[5]
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6]
A proline-catalyzed asymmetric Robinson annulation reaction
[J].
Bui, T
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Bui, T
;
Barbas, CF
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Barbas, CF
.
TETRAHEDRON LETTERS,
2000,
41
(36)
:6951
-6954
[7]
Asymmetric aldol reaction using immobilized proline on mesoporous support
[J].
Calderón, F
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Calderón, F
;
Fernández, R
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Fernández, R
;
Sánchez, F
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Sánchez, F
;
Fernández-Mayoralas, A
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
Fernández-Mayoralas, A
.
ADVANCED SYNTHESIS & CATALYSIS,
2005,
347
(10)
:1395
-1403
[8]
Synthesis of azasugars through a proline-catalyzed reaction
[J].
Calderon, Felix
论文数:
0
引用数:
0
h-index:
0
机构:
Instituto de Química Orgánica General, C/Juan de la Cierva
Calderon, Felix
;
Doyaguez, Elisa G.
论文数:
0
引用数:
0
h-index:
0
机构:
Instituto de Química Orgánica General, C/Juan de la Cierva
Doyaguez, Elisa G.
;
Fernandez-Mayoralas, Alfonso
论文数:
0
引用数:
0
h-index:
0
机构:
Instituto de Química Orgánica General, C/Juan de la Cierva
Fernandez-Mayoralas, Alfonso
.
JOURNAL OF ORGANIC CHEMISTRY,
2006,
71
(16)
:6258
-6261
[9]
Pipecolic acid-catalyzed direct asymmetric Mannich reactions
[J].
Cheong, PHY
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Cheong, PHY
;
Zhang, HL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Zhang, HL
;
Thayumanavan, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Thayumanavan, R
;
Tanaka, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Tanaka, F
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
;
Barbas, CF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Barbas, CF
.
ORGANIC LETTERS,
2006,
8
(05)
:811
-814
[10]
Computational evidence for the enamine mechanism of intramolecular Aldol reactions catalyzed by proline
[J].
Clemente, FR
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Clemente, FR
;
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004,
43
(43)
:5766
-5768
←
1
2
3
→