LITHIUM-AMMONIA CLEAVAGE OF THE N-N BOND IN N-(METHOXYCARBONYL)-ACETYLHYDRAZINES AND N-ACETYLHYDRAZINES

被引：90

作者：

DENMARK, SE

NICAISE, O

EDWARDS, JP

机构：

[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 25期

关键词：

D O I：

10.1021/jo00312a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective addition of organocerium reagents to L-proline-derived hydrazones 1 has recently been reported from these laboratories1(Scheme I). The reaction is compatible with a wide range of substrates (R1= Ph, PhCH2,PhCH2CH2, (E)-CH3CH=CH) and accommodates a variety of unstabilized nucleophiles (R3= Me, n-Bu, i-Pr, t-Bu, Ph, i-Pr3SiCH=CH) derived from either lithium or halomagnesium precursors. The additions proceed in good yield (67-81%) and with high diastereoselectivity (>93:7 ds). © 1990, American Chemical Society. All rights reserved.

引用

页码：6219 / 6223

页数：5

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