Diastereoselection in rhodium-mediated intramolecular CH insertion: preparation of a trans-3, 4 dialkyl cyclopentane

DF Taber, RE Ruckle

Index: Taber, Douglass F.; Ruckle, Robert E. Tetrahedron Letters, 1985 , vol. 26, # 26 p. 3059 - 3062

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Citation Number: 47

Abstract

Transition state analysis suggests that substantial 1,2 asymmetric induction could be observed in the course of rhodium-mediated intramolecular CH insertion. This analysis successfully predicts predominant formation of the 3,4-dialkyl cyclopentane when an α-diazo β-ketoester having a δ-phenyl substituent is cyclized. ... TLC R f (20% EtOAc/hexane) = 0.33; IR: 2965, 1740, 1730, 1500, 1460, 1440, 1410, 1330, 1295, 1205, 1145, 1040, 695 cm −1 ; 1 H NMR: ...