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

被引：362

作者：

Lalonde, Mathieu P. ^{[1
]}

Chen, Yonggang ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 38期

关键词：

amines; asymmetric catalysis; conjugate addition; organocatalysis;

D O I：

10.1002/anie.200602221

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Dual activation: The bifunctional primary amine thiourea catalyst 1 promotes the highly enantioselective direct conjugate addition of α-branched aldehydes to nitroalkenes (see scheme). Cooperative activation of both the nucleophile and electrophile allows the use of mild reaction conditions and provides access to a wide variety of adducts with vicinal quaternary and tertiary stereogenic centers (>90% ee). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6366 / 6370

页数：5

共 91 条

[61] Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea [J].

Okino, T ;

Hoashi, Y ;

Furukawa, T ;

Xu, XN ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :119-125

[62] Enantioselective Aza-Henry reaction catalyzed by a bifunctional organocatalyst [J].

Okino, T ;

Nakamura, S ;

Furukawa, T ;

Takemoto, Y .

ORGANIC LETTERS, 2004, 6 (04) :625-627

[63] Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts [J].

Okino, T ;

Hoashi, Y ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12672-12673

[64]

PFAU M, 1970, J CHEM SOC CHEM COMM, P66

[65] Prebiotic amino acids as asymmetric catalysts [J].

Pizzarello, S ;

Weber, AL .

SCIENCE, 2004, 303 (5661) :1151-1151

[66]

RISALITI A, 1966, TETRAHEDRON LETT, P6331

[67]

RISALITI A, 1966, TETRAHEDRON LETT, P1821

[68] Metal-free organocatalysis through explicit hydrogen bonding interactions [J].

Schreiner, PR .

CHEMICAL SOCIETY REVIEWS, 2003, 32 (05) :289-296

[69] ON THE STERIC COURSE OF THE REACTION OF ENAMINES DERIVED FROM OPEN-CHAIN ALDEHYDES AND KETONES WITH NITRO-OLEFINS YIELDING 2,3-DISUBSTITUTED 4-NITROKETONES [J].

SEEBACH, D ;

BECK, AK ;

GOLINSKI, J ;

HAY, JN ;

LAUBE, T .

HELVETICA CHIMICA ACTA, 1985, 68 (01) :162-172

[70] SYNTHESIS OF OPEN-CHAIN 2,3-DISUBSTITUTED 4-NITROKETONES BY DIASTEREOSELECTIVE MICHAEL-ADDITION OF (E)-ENAMINES TO (E)-NITROOLEFINS - A TOPOLOGICAL RULE FOR C,C-BOND FORMING PROCESSES BETWEEN PROCHIRAL CENTERS [J].

SEEBACH, D ;

GOLINSKI, J .

HELVETICA CHIMICA ACTA, 1981, 64 (05) :1413-1423

← 1 2 3 4 5 6 7 8 9 10 →