Stereoselective synthesis of α-silylamines by the direct addition of silyl anions to activated Imines

被引：49

作者：

Ballweg, DM ^{[1
]}

Miller, RC ^{[1
]}

Gray, DL ^{[1
]}

Scheidt, KA ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol050244u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient stereoselective synthesis of unusual alpha-silylamines via a direct silyl anion addition reaction is reported. This approach is convergent and avoids any problematic aza-Brook shifts of the anionic intermediates. The use of enantiopure tert-butanesulfinyl imines as the electrophiles affords exceedingly high levels of diastereocontrol for the newly formed stereogenic carbon.

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页码：1403 / 1406

页数：4

相关论文

共 39 条

[1] MECHANISM OF INACTIVATION OF MONOAMINE OXIDASE-B BY (AMINOMETHYL)TRIMETHYLSILANE [J].

BANIK, GM ;

SILVERMAN, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4499-4507

[2] Preparation of enantioenriched α-silyl-benzylcarbamates [J].

Barberis, C ;

Voyer, N .

TETRAHEDRON LETTERS, 1998, 39 (38) :6807-6810

[3]

Bolm C, 2000, ANGEW CHEM INT EDIT, V39, P2288, DOI 10.1002/1521-3773(20000703)39:13<2288::AID-ANIE2288>3.0.CO

[4]

2-Y

[5] Stereoselective three-carbon and two-carbon elongation of the carbon chain in N-boc-protected α-aminoacylsilanes:: An entry to functionalized β-amino alcohols and to statine analogues [J].

Bonini, BF ;

Comes-Franchini, M ;

Fochi, M ;

Laboroi, F ;

Mazzanti, G ;

Ricci, A ;

Varchi, G .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :8008-8013

[6] Drug design with a new transition state analog of the hydrated carbonyl: silicon-based inhibitors of the HIV protease [J].

Chen, CA ;

Sieburth, SM ;

Glekas, A ;

Hewitt, GW ;

Trainor, GL ;

Erickson-Viitanen, S ;

Garber, SS ;

Cordova, B ;

Jeffry, S ;

Klabe, RM .

CHEMISTRY & BIOLOGY, 2001, 8 (12) :1161-1166

[7] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C ;

YOUNG, JC .

CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448

[8] Efficient synthesis of acylsilanes using morpholine amides [J].

Clark, CT ;

Milgram, BC ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (22) :3977-3980

[9] Copper(I)-catalyzed disilylation of alkylidene malonates employing a Lewis base activation strategy [J].

Clark, CT ;

Lake, JF ;

Scheidt, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) :84-85

[10] Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].

Cogan, DA ;

Liu, GC ;

Ellman, J .

TETRAHEDRON, 1999, 55 (29) :8883-8904

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