DIRHODIUM(II) TETRA(TRIPHENYLACETATE) - A HIGHLY EFFICIENT CATALYST FOR THE SITE-SELECTIVE INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-DIAZO BETA-KETO-ESTERS

被引：101

作者：

HASHIMOTO, S ^{[1
]}

WATANABE, N ^{[1
]}

IKEGAMI, S ^{[1
]}

机构：

[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)79063-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dirhodium(II) tetra(triphenylacetate), Rh2(TPA)4, featured by a bulky bridging ligand has been demonstrated to exhibit an exceptionally high order of selectivity for C-H insertion into methylene over methine in catalytic decompositions of alpha-diazo beta-keto esters tethered to a cyclic system, thus providing an expedient and general entry to bicyclic compounds in preference to spirocyclic compounds. The efficiency is verified well by high-yield and site-controlled construction of bicyclo[3.3.0]octane derivative, a pivotal intermediate for the convergent synthesis of (+)-isocarbacyclin.

引用

页码：2709 / 2712

页数：4

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