Asymmetric organocatalytic conjugate addition of malonates to enones using a proline tetrazole catalyst

被引：168

作者：

Knudsen, KR ^{[1
]}

Mitchell, CET ^{[1
]}

Ley, SV ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

CHEMICAL COMMUNICATIONS | 2006年 / 01期

关键词：

D O I：

10.1039/b514636d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

5-Pyrrolidin-2-yltetrazole performs as a useful organocatalyst for the asymmetric addition of malonates to a range of enones, with good to excellent enantioselectivities.

引用

页码：66 / 68

页数：3

共 29 条

[1]

Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259

[2] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].

Cobb, AJA ;

Shaw, DM ;

Longbottom, DA ;

Gold, JB ;

Ley, SV .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96

[3] 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins [J].

Cobb, AJA ;

Longbottom, DA ;

Shaw, DM ;

Ley, SV .

CHEMICAL COMMUNICATIONS, 2004, (16) :1808-1809

[4] 5-pyrrolidin-2-yltetrazole: A new, catalytic, more soluble alternative to proline in an organocatalytic asymmetric Mannich-type reaction [J].

Cobb, AJA ;

Shaw, DM ;

Ley, SV .

SYNLETT, 2004, (03) :558-560

[5] Organocatalytic transformation of 1,3-diketones into optically active cyclohexanones [J].

Gryko, D .

TETRAHEDRON-ASYMMETRY, 2005, 16 (07) :1377-1383

[6] Highly enantioselective organocatalytic conjugate addition of malonates to acyclic α,β-unsaturated enones [J].

Halland, N ;

Aburel, PS ;

Jorgensen, KA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (06) :661-665

[7] Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones [J].

Hanessian, S ;

Pham, V .

ORGANIC LETTERS, 2000, 2 (19) :2975-2978

[8] Rational design of asymmetric organocatalysts - increased reactivity and solvent scope with a tetrazolic acid [J].

Hartikka, A ;

Arvidsson, PI .

TETRAHEDRON-ASYMMETRY, 2004, 15 (12) :1831-1834

[9] Enantioselective Michael addition to α,β-unsaturated imides catalyzed by a bifunctional organocatalyst [J].

Hoashi, Y ;

Okino, T ;

Takemoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4032-4035

[10] SYNTHETIC APPLICATIONS OF DEALKOXYCARBONYLATIONS OF MALONATE ESTERS, BETA-KETO-ESTERS, ALPHA-CYANO ESTERS AND RELATED-COMPOUNDS IN DIPOLAR APROTIC MEDIA .2. [J].

KRAPCHO, AP .

SYNTHESIS-STUTTGART, 1982, (11) :893-914

← 1 2 3 →