A highly practical and enantioselective reagent for the allylation of aldehydes

被引：130

作者：

Kubota, K ^{[1
]}

Leighton, JL ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 08期

关键词：

D O I：

10.1002/anie.200390252

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Strain at silicon is the key to success of reagent 1 since this strain, which is induced by the diazasilacyclopentane ring, determines its reactivity. This practical and general new reagent for the highly enantioselective allylation of aldehydes is easily prepared as an air-stable solid and may be stored without significant decomposition.

引用

收藏

页码：946 / +

页数：4

相关论文

共 27 条

[11] ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYL ALCOHOLS VIA CHIRAL ALLYLBORONIC ESTERS [J].

HEROLD, T ;

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (10) :768-769

[12]

Herold T., 1978, ANGEW CHEM, V90, P822

[13] A chiral formamide: Design and application to catalytic asymmetric synthesis [J].

Iseki, K ;

Mizuno, S ;

Kuroki, Y ;

Kobayashi, Y .

TETRAHEDRON LETTERS, 1998, 39 (18) :2767-2770

[14] Asymmetric allylation of aldehydes catalyzed by substoichiometric amounts of chiral phosphoramides [J].

Iseki, K ;

Kuroki, Y ;

Takahashi, M ;

Kobayashi, Y .

TETRAHEDRON LETTERS, 1996, 37 (29) :5149-5150

[15] Asymmetric allylation with chiral formamide catalysts [J].

Iseki, K ;

Mizuno, S ;

Kuroki, Y ;

Kobayashi, Y .

TETRAHEDRON, 1999, 55 (04) :977-988

[16] Asymmetric allylation of aromatic aldehydes catalyzed by chiral phosphoramides prepared from (S)-proline [J].

Iseki, K ;

Kuroki, Y ;

Takahashi, M ;

Kishimoto, S ;

Kobayashi, Y .

TETRAHEDRON, 1997, 53 (10) :3513-3526

[17] CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS [J].

JADHAV, PK ;

BHAT, KS ;

PERUMAL, PT ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :432-439

[18] Strained silacycles in organic synthesis: A new reagent for the enantioselective allylation of aldehydes [J].

Kinnaird, JWA ;

Ng, PY ;

Kubota, K ;

Wang, XL ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7920-7921

[19] Chiral 2,2′-bipyridine-type N-monoxides as organocatalysts in the enantioselective allylation of aldehydes with allyltrichlorosilane [J].

Malkov, AV ;

Orsini, M ;

Pernazza, D ;

Muir, KW ;

Langer, V ;

Meghani, P ;

Kocovsky, P .

ORGANIC LETTERS, 2002, 4 (06) :1047-1049

[20] (S)-3,3′-dimethyl-2,2′-biquinoline N,N′-dioxide as an efficient catalyst for enantioselective addition of allyltrichlorosilanes to aldehydes [J].

Nakajima, M ;

Saito, M ;

Shiro, M ;

Hashimoto, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (25) :6419-6420