Allyldimethyltritylsilane:: construction of enantiomerically pure cyclobutano[c]fused pyrrolidines

被引：12

作者：

Groaning, MD ^{[1
]}

Brengel, GP ^{[1
]}

Meyers, AI ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 13期

基金：

美国国家卫生研究院;

关键词：

cyclobutannulation; allyldimethyltritylsilane; '[2+2]' cycloaddition;

D O I：

10.1016/S0040-4020(01)00083-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclobutannulation of the bicyclic lactam with allyldimethyltritylsilane is accomplished in high yield with good diastereoselectivity. The resulting tricyclic system is converted to a enantiomerically pure cyclobutane-fused pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2635 / 2642

页数：8

共 46 条

[1] Stereoselective synthesis of cyclopentanols by Lewis acid-mediated [3+2] annulation of allyldiisopropylphenylsilane with α,β-unsaturated diesters [J].

Akiyama, T ;

Yamanaka, M .

TETRAHEDRON LETTERS, 1998, 39 (43) :7885-7888

[2] ASYMMETRIC-SYNTHESIS OF TETRAHYDROFURANS BY DIASTEREOSELECTIVE [3+2]-CYCLOADDITION OF ALLYLSILANES WITH ALPHA-KETO ESTERS BEARING AN OPTICALLY-ACTIVE CYCLITOL AS A CHIRAL AUXILIARY [J].

AKIYAMA, T ;

YASUSA, T ;

ISHIKAWA, K ;

OZAKI, S .

TETRAHEDRON LETTERS, 1994, 35 (45) :8401-8404

[3]

Akiyama T, 1996, SYNLETT, P1095

[4] ASYMMETRIC CONJUGATE ADDITIONS TO CHIRAL BICYCLIC LACTAMS - A STEREOSELECTIVE, CONCISE SYNTHESIS OF CHIRAL 2-ALKYL-3,4-AZIRIDINOPYRROLIDINES [J].

ANDRES, CJ ;

MEYERS, AI .

TETRAHEDRON LETTERS, 1995, 36 (20) :3491-3494

[5] FORMAL [3+3]-CYCLOADDITIONS AND [3+2]-CYCLOADDITIONS OF ALLYLSILANES WITH BENZYLIC CATIONS [J].

ANGLE, SR ;

BOYCE, JP .

TETRAHEDRON LETTERS, 1994, 35 (35) :6461-6464

[6] A NEW SYNTHESIS OF SUBSTITUTED AZULENES [J].

BECKER, DA ;

DANHEISER, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :389-391

[7] Tritylallyldimethylsilane-TiCl4 annulations to electron deficient olefins. Diastereomerically pure 3-substituted and 3,4-disubstituted cyclopentanols [J].

Brengel, GP ;

Meyers, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3230-3231

[8] PEROXIDES OF ELEMENTS OTHER THAN CARBON .1. THE PREPARATION AND REACTIONS OF PEROXYSILANES [J].

BUNCEL, E ;

DAVIES, AG .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (APR) :1550-1556

[9] A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES [J].

BURGESS, LE ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1656-1662

[10] APPLICATION OF ALLENYLSILANES IN [3 + 2] ANNULATION APPROACHES TO OXYGEN AND NITROGEN-HETEROCYCLES [J].

DANHEISER, RL ;

KWASIGROCH, CA ;

TSAI, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7233-7235

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