Chelation control through the coordination of an olefinic π-bond to Lewis acid

被引：7

作者：

Asao, N ^{[1
]}

Shimada, T ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 49期

关键词：

chelation; alkenes; Lewis acid; carbonyl compounds; reduction; allylation;

D O I：

10.1016/S0040-4039(00)01667-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of a 1:1 mixture of ortho-alkenylbenzaldehydes 3 and their para-isomers 4 with Bu3SnH (1 equiv.) in the presence of Me3Al (1 equiv.) resulted in very high (>10:1) to good (3.4:1) chemoselective reduction of 3, giving the ortho-alkenyl benzyl alcohol 5 selectively. Similarly, the highly chemoselective allylation of 3d in the presence of 4d was observed when the mixture was treated with allyltributyltin/Me3Al. The chemoselectivities are most probably due to the bidentate chelation of the Lewis acid to an olefinic pi -bond and a lone pair of aldehydes. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：9533 / 9536

页数：4

共 20 条

[1]

AAO N, 2000, J AM CHEM SOC, V122, P4817

[2]

[Anonymous], COMPREHENSIVE ORGANI

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