共 55 条
Catalytic asymmetric three-component acyl-Strecker reaction
被引:93
作者:

Pan, Subhas Chandra
论文数: 0 引用数: 0
h-index: 0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

List, Benjamin
论文数: 0 引用数: 0
h-index: 0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
机构:
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词:
D O I:
10.1021/ol0702674
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The first organocatalytic asymmetric three-component Strecker reaction, the urea-catalyzed acylcyanation of in situ generated imines, has been developed. Different alpha-amido nitriles are formed in excellent yields and enantioslectivities from aldehydes, amines, and acyl cyanides in the presence of Jacobsen's thiourea catalyst 5. Despite its obvious use for the synthesis of alpha-amino acids and their derivatives, our reaction may find use in diversity oriented synthesis and medicinal chemistry.
引用
收藏
页码:1149 / 1151
页数:3
相关论文
共 55 条
[1]
Recent progress in chiral Bronsted acid catalysis
[J].
Akiyama, Takahiko
;
Itoh, Junji
;
Fuchibe, Kohei
.
ADVANCED SYNTHESIS & CATALYSIS,
2006, 348 (09)
:999-1010

Akiyama, Takahiko
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Itoh, Junji
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Fuchibe, Kohei
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
[2]
Asymmetric synthesis of O-benzoyl cyanohydrins by reaction of aldehydes with benzoyl cyanide catalysed by BINOLAM-Ti(IV) complexes
[J].
Baeza, A
;
Nájera, C
;
Sansano, JM
;
Saá, JM
.
TETRAHEDRON-ASYMMETRY,
2005, 16 (14)
:2385-2389

Baeza, A
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

Nájera, C
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

Sansano, JM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

Saá, JM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain
[3]
A highly enantioselective Strecker reaction catalyzed by titanium-N-salicyl-β-aminoalcohol complexes
[J].
Banphavichit, V
;
Mansawat, W
;
Bhanthumnavin, W
;
Vilaivan, T
.
TETRAHEDRON,
2004, 60 (46)
:10559-10568

Banphavichit, V
论文数: 0 引用数: 0
h-index: 0
机构:
Chulalongkorn Univ, Fac Sci, Dept Chem, Organ Synthesis Res Unit, Bangkok 10330, Thailand Chulalongkorn Univ, Fac Sci, Dept Chem, Organ Synthesis Res Unit, Bangkok 10330, Thailand

Mansawat, W
论文数: 0 引用数: 0
h-index: 0
机构:
Chulalongkorn Univ, Fac Sci, Dept Chem, Organ Synthesis Res Unit, Bangkok 10330, Thailand Chulalongkorn Univ, Fac Sci, Dept Chem, Organ Synthesis Res Unit, Bangkok 10330, Thailand

论文数: 引用数:
h-index:
机构:

论文数: 引用数:
h-index:
机构:
[4]
Cyanide ion cocatalysis in Ti(salen) catalysed asymmetric cyanohydrin carbonate synthesis
[J].
Belokon, YN
;
Ishibashi, E
;
Nomura, H
;
North, M
.
CHEMICAL COMMUNICATIONS,
2006, (16)
:1775-1777

Belokon, YN
论文数: 0 引用数: 0
h-index: 0
机构: Univ Newcastle, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

Ishibashi, E
论文数: 0 引用数: 0
h-index: 0
机构: Univ Newcastle, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

Nomura, H
论文数: 0 引用数: 0
h-index: 0
机构: Univ Newcastle, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

North, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Newcastle, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
[5]
Catalytic, asymmetric synthesis of cyanohydrin ethyl carbonates
[J].
Belokon, YN
;
Blacker, AJ
;
Clutterbuck, LA
;
North, M
.
ORGANIC LETTERS,
2003, 5 (23)
:4505-4507

Belokon, YN
论文数: 0 引用数: 0
h-index: 0
机构: Kings Coll London, Dept Chem, London WC2R 2LS, England

Blacker, AJ
论文数: 0 引用数: 0
h-index: 0
机构: Kings Coll London, Dept Chem, London WC2R 2LS, England

Clutterbuck, LA
论文数: 0 引用数: 0
h-index: 0
机构: Kings Coll London, Dept Chem, London WC2R 2LS, England

North, M
论文数: 0 引用数: 0
h-index: 0
机构:
Kings Coll London, Dept Chem, London WC2R 2LS, England Kings Coll London, Dept Chem, London WC2R 2LS, England
[6]
Reversal of enantioselectivity by catalyst protonation: Asymmetric hydrocyanation of imines with oxazaborolidines
[J].
Berkessel, A
;
Mukherjee, S
;
Lex, J
.
SYNLETT,
2006, (01)
:41-44

Berkessel, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

Mukherjee, S
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

Lex, J
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
[7]
Enantioselective cyanoformylation of aldehydes mediated by BINOLAM-AlCl as a monometallic bifunctional catalyst
[J].
Casas, J
;
Baeza, A
;
Sansano, JM
;
Nájera, C
;
Saá, JM
.
TETRAHEDRON-ASYMMETRY,
2003, 14 (02)
:197-200

Casas, J
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

论文数: 引用数:
h-index:
机构:

Sansano, JM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

Nájera, C
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

Saá, JM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain
[8]
Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines
[J].
Connon, Stephen J.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006, 45 (24)
:3909-3912

Connon, Stephen J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Dublin Trinity Coll, Dept Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland Univ Dublin Trinity Coll, Dept Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
[9]
Organocatalysis mediated by (thio)urea derivatives
[J].
Connon, Stephen J.
.
CHEMISTRY-A EUROPEAN JOURNAL,
2006, 12 (21)
:5418-5427

Connon, Stephen J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
[10]
Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst
[J].
Corey, EJ
;
Grogan, MJ
.
ORGANIC LETTERS,
1999, 1 (01)
:157-160

Corey, EJ
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Grogan, MJ
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA