An unexpected reversal of diastereoselectivity in the [4+3]-cycloaddition reaction of nitrogen-stabilized oxyallyl cations with methyl 2-furoate

被引：25

作者：

Antoline, Jennifer E.

Hsung, Richard P.

机构：

[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA

[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA

来源：

SYNLETT | 2008年 / 05期

关键词：

stereoselective [4+3] cycloadditions; allenamides; nitrogen-stabilized oxyallyl cations; endo-I versus endo-II selectivity; dipole interaction;

D O I：

10.1055/s-2008-1042765

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unexpected reversal of diastereoselectivity in the [4+3] cycloaddition of methyl 2-fuorate with nitrogen-stabilized oxyallyl cations derived from epoxidation of chiral allenamides is described here. This intriguing reversal in favor of the endo-H cycloaddition pathway is likely a result of minimizing the dipole interaction between the oxyallyl cation and ester carbonyl of methyl 2-fuorate.

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收藏

页码：739 / 744

页数：6

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