Copper-Catalyzed Conjugate Additions of Alkylboranes to Imidazolyl α,β-Unsaturated Ketones: Formal Reductive Conjugate Addition of Terminal Alkenes

被引：34

作者：

Ohmiya, Hirohisa ^{[1
]}

Yoshida, Mika ^{[1
]}

Sawamura, Masaya ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 03期

关键词：

N-HETEROCYCLIC CARBENES; CARBONYL-COMPOUNDS; ARYLBORONIC ACIDS; GRIGNARD-REAGENTS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC 1,4-ADDITION; DIORGANOZINC REAGENTS; DIASTEREOSELECTIVE SYNTHESIS; SUBSTITUTION-REACTIONS; TRISUBSTITUTED ENONES;

D O I：

10.1021/ol102819k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition of alkylboron compounds (allryl-9-BBN) to imidazol-2-yl alpha,beta-unsaturated ketones proceeded in the presence of a catalytic amount (10 mol %) of CuCl, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes), and t-BuOK. The alkylboranes are available through alkene hydroboration, and thus the overall process represents a reductive conjugate addition of alkenes to enone derivatives. A variety of functional groups are tolerated in both the alkenes and the alpha,beta-unsaturated ketones. The 2-acylimidazole moiety can easily be converted into the corresponding carboxylic acid, ester, and amide derivatives.

引用

页码：482 / 485

页数：4

共 65 条

[31] Krause N., 2001, SYNTHESIS-STUTTGART, V171, P196
[32] Efficient homogeneous catalysis in the reduction of CO2 to CO
Laitar, DS
Müller, P
Sadighi, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) : 17196 - 17197
[33] Preparation of functionalized dialkylzincs via a boron-zinc exchange. Reactivity and catalytic asymmetric addition to aldehydes
Langer, F
Schwink, L
Devasagayaraj, A
Chavant, PY
Knochel, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8229 - 8243
[34] A practical method for enantioselective synthesis of all-carbon quaternary stereogenic centers through NHC-Cu-catalyzed conjugate additions of alkyl- and arylzinc reagents to β-substituted cyclic enones
Lee, Kang-Sang
Brown, M. Kevin
Hird, Alexander W.
Hoveyda, Amir H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) : 7182 - 7184
[35] Enantioselective Conjugate Silyl Additions to Cyclic and Acyclic Unsaturated Carbonyls Catalyzed by Cu Complexes of Chiral N-Heterocyclic Carbenes
Lee, Kang-sang
Hoveyda, Amir H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 2898 - +
[36] Vicinal Diboronates in High Enantiomeric Purity through Tandem Site-Selective NHC-Cu-Catalyzed Boron-Copper Additions to Terminal Alkynes
Lee, Yunmi
Jang, Hwanjong
Hoveyda, Amir H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (51) : 18234 - +
[37] Efficient Boron-Copper Additions to Aryl-Substituted Alkenes Promoted by NHC-Based Catalysts. Enantioselective Cu-Catalyzed Hydroboration Reactions
Lee, Yunmi
Hoveyda, Amir H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) : 3160 - +
[38] Palladium-bipyridine catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carbonyl compounds in aqueous media
Lin, Shaohui
Lu, Xiyan
[J]. TETRAHEDRON LETTERS, 2006, 47 (40) : 7167 - 7170
[39] Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon Centers
Lin, Shaohui
Lu, Xiyan
[J]. ORGANIC LETTERS, 2010, 12 (11) : 2536 - 2539
[40] HYDROZIRCONATION-TRANSMETALATION - A MILD, DIRECT ROUTE TO HIGHER-ORDER VINYLIC CUPRATES FROM MONOSUBSTITUTED ACETYLENES
LIPSHUTZ, BH
ELLSWORTH, EL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) : 7440 - 7441

← 1 2 3 4 5 6 7 →