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.
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页码：2709 / 2712
页数：4
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