Tetrahedron: Asymmetry

Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

JD Moore, PR Hanson

Index: Moore, Joel D.; Hanson, Paul R. Tetrahedron Asymmetry, 2003 , vol. 14, # 7 p. 873 - 880

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Citation Number: 13

Abstract

The investigation of substituent effects in the double diastereotopic differentiation of substituted α-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh2 (OAc) 4 is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways:(i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or ( ...