Tetrahedron: Asymmetry

Synthesis and characterization of both enantiomers of trans-1, 2-di-(2-hydroxy-2-propyl)-cyclobutane

FW Curtius, HD Scharf

Index: Curtius, Frank W.; Scharf, Hans-Dieter Tetrahedron Asymmetry, 1996 , vol. 7, # 10 p. 2957 - 2961

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Citation Number: 21

Abstract

Both enantiomers of the title compound are synthesized for the first time in four steps including a [2+ 2]-photocycloaddition to build up the cyclobutane backbone and a cerium supported reductive permethylation. During the cerium supported process a complete and selective change in the configuration of the cyclobutane ring takes place. The substituents are transformed from the cis-to the trans-geometry.