Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent

被引：50

作者：

Chan, KP ^{[1
]}

Loh, TP ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 45期

关键词：

tetrahydropyran; Prins cyclization; In(OTf)(3); InCl3;

D O I：

10.1016/j.tetlet.2004.09.049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with alpha,beta-unsaturated aldehydes affording moderate yields of products. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8387 / 8390

页数：4

共 17 条

[1]

ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661

[2] THE OLEFIN ALDEHYDE CONDENSATION - THE PRINS REACTION [J].

ARUNDALE, E ;

MIKESKA, LA .

CHEMICAL REVIEWS, 1952, 51 (03) :505-555

[3] SYNTHESIS OF 4-HALOTETRAHYDROPYRANS FROM ALLYLSILANES AND CARBONYL-COMPOUNDS IN THE PRESENCE OF LEWIS-ACIDS [J].

COPPI, L ;

RICCI, A ;

TADDEI, M .

TETRAHEDRON LETTERS, 1987, 28 (09) :973-976

[4]

COPPI L, 1988, J ORG CHEM, V53, P913

[5] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

[6] THE STEREOCHEMISTRY OF SOME SE2' REACTIONS OF ALLYLSILANES AND ALLENYLSILANES [J].

FLEMING, I ;

TERRETT, NK .

TETRAHEDRON LETTERS, 1983, 24 (38) :4153-4156

[7]

HAYASHI T, 1982, J AM CHEM SOC, V104, P4963, DOI 10.1021/ja00382a046

[8] CHEMISTRY OF ORGANOSILICON COMPOUNDS .99. CONJUGATE ADDITION OF ALLYLSILANES TO ALPHA, BETA-ENONES - NEW METHOD OF STEREOSELECTIVE INTRODUCTION OF ANGULAR ALLYL GROUP IN FUSED CYCLIC ALPHA, BETA-ENONES [J].

HOSOMI, A ;

SAKURAI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1673-1675

[9]

HOSOMI A, 1976, TETRAHEDRON LETT, P1295

[10]

Li C. -J., 1997, ORGANIC REACTIONS AQ

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