Addition of benzyltrimethylsilane to imines triggered by tetrabutylammonium fluoride

被引：23

作者：

Zhang, Wan-Xuan

Ding, Chang-Hua

Luo, Zhi-Bin

Hou, Xue-Long

Dai, Li-Xin

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China

[3] Hunei Univ, Fac Chem & Mat Sci, Wuhan 430062, Peoples R China

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 47期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetlet.2006.09.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of benzyltrimethylsilane 2 to imines 1 triggered by TBAF in the presence of 4A molecular sieves gave rise to the corresponding alpha-benzylated amines 3 in good yields. Moderate to high diastereoselectivity was obtained in the reactions of tert-butanesulfinyl imines with 2. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8391 / 8393

页数：3

共 15 条

[1] A NEW ORGANOSILICIATED SYNTONE - BENZYLTRIMETHYLSILANE [J].

BENNETAU, B ;

DUNOGUES, J .

TETRAHEDRON LETTERS, 1983, 24 (39) :4217-4218

[2]

Challener C.A., 2001, CHIRAL DRUGS

[3] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[4] The first catalytic asymmetric allylation of imines with the tetraallylsilane-TBAF-MeOH system, using the chiral bis-π-allylpalladium complex [J].

Fernandes, RA ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :735-738

[5] Development of new reagents containing silicon and related metals and application to practical organic syntheses [J].

Hosomi, A ;

Miura, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (05) :835-851

[6]

HOSOMI A, 1978, TETRAHEDRON LETT, P3043

[7] REGIOSPECIFIC AND DIASTEREOSELECTIVE CROTYLATION OF ALDIMINES WITH CROTYLTRIFLUOROSILANES ACTIVATED BY FLUORIDE IONS [J].

KIRA, M ;

HINO, T ;

SAKURAI, H .

CHEMISTRY LETTERS, 1991, (02) :277-280

[8] Characterization of a stable ruthenium complex with an oxyl radical [J].

Kobayashi, K ;

Ohtsu, H ;

Wada, T ;

Kato, T ;

Tanaka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6729-6739

[9] CHEMISTRY OF IMINES [J].

LAYER, RW .

CHEMICAL REVIEWS, 1963, 63 (05) :489-+

[10] Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyltrichlorosilanes:: The role of arene-arene interactions [J].

Malkov, AV ;

Dufková, L ;

Farrugia, L ;

Kocovsky, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3674-3677

← 1 2 →