STEREOSELECTIVITY IN THE HOMO-DIELS-ALDER REACTION - EFFECT OF A REMOTE 7-SUBSTITUENT ON NICKEL-CATALYZED CYCLOADDITIONS

被引：28

作者：

LAUTENS, M

TAM, W

EDWARDS, LG

机构：

[1] Department of Chemistry, University of Toronto, Toronto

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 15期

关键词：

D O I：

10.1039/p19940002143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

7-Substituted norbornadienes have been shown to undergo highly stereoselective homo-Diels-Alder reactions with a variety of dienophiles. Excellent exo/endo selectivity (always >97:3) was observed when methyl vinyl ketone was used as dienophile. Increasing anti/syn selectivity (up to 95:5 when Y = OBu(t)) was observed as the electronegativity of the 7-substituent increased.

引用

页码：2143 / 2150

页数：8

共 37 条

[1]

ASTIN KB, 1975, J CHEM SOC P2, P1005

[2]

BATTISTE MA, 1976, TETRAHEDRON LETT, P2529

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