Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with β-nitroalkenes

被引：64

作者：

Sato, Atsushi ^{[1
]}

Yoshida, Masanori ^{[1
]}

Hara, Shoji ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 46期

关键词：

D O I：

10.1039/b814804j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Phenylalanine lithium salt was found to be an effective catalyst for asymmetric Michael addition of isobutyraldehyde with beta-nitroalkenes to give quaternary carbon-containing nitroalkanes.

引用

页码：6242 / 6244

页数：3

共 35 条

[11] Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst [J].

Huang, Hongbing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7170-7171

[12] A chiral primary amine thiourea catalyst for the highly enantioselective direct conjugate addition of α,α-disubstituted aldehydes to nitroalkenes [J].

Lalonde, Mathieu P. ;

Chen, Yonggang ;

Jacobsen, Eric N. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (38) :6366-6370

[13] Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition [J].

Li, HM ;

Wang, Y ;

Tang, L ;

Wu, FH ;

Liu, XF ;

Guo, CY ;

Foxman, BM ;

Deng, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :105-108

[14] Effective and recyclable dendritic catalysts for the direct asymmetric Michael addition of aldehydes to nitrostyrenes [J].

Li, Yawen ;

Liu, Xin-Yuan ;

Zhao, Gang .

TETRAHEDRON-ASYMMETRY, 2006, 17 (13) :2034-2039

[15] Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins [J].

Luo, Sanzhong ;

Mi, Xueling ;

Zhang, Long ;

Liu, Song ;

Xu, Hui ;

Cheng, Jin-Pei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3093-3097

[16] Synthesis of prolinal dithioacetals as catalysts for the highly stereoselective Michael addition of ketones and aldehydes to β-nitrostyrenes [J].

Mandal, Tanmay ;

Zhao, Cong-Gul .

TETRAHEDRON LETTERS, 2007, 48 (33) :5803-5806

[17] Organocatalytic direct Michael reaction of ketones and aldehydes with β-nitrostyrene in brine [J].

Mase, N ;

Watanabe, K ;

Yoda, H ;

Takabe, K ;

Tanaka, F ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4966-4967

[18] Direct asymmetric organocatalytic Michael reactions of α,α-disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products [J].

Mase, N ;

Thayumanavan, R ;

Tanaka, F ;

Barbas, CF .

ORGANIC LETTERS, 2004, 6 (15) :2527-2530

[19] Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins [J].

McCooey, Seamus H. ;

Connon, Stephen J. .

ORGANIC LETTERS, 2007, 9 (04) :599-602

[20] Organocatalyzed asymmetric reactions via microwave activation [J].

Mosse, Sarah ;

Alexakis, Alexandre .

ORGANIC LETTERS, 2006, 8 (16) :3577-3580

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