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

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...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 7; no. 10; pp. 2957 - 2961
Main Authors Curtius, Frank W., Scharf, Hans-Dieter
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.10.1996
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
CHIRAL INDUCTION
ACID
PHOTOCHEMICAL-REACTIONS
DERIVATIVES
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Summary: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. An asymmetric four step preparation of the enantiomerically pure trans-1,2-Di-(2-hydroxy-2-propyl)-cyclobutanes 6 and ent-6 via intermediate 4a is described. [Display omitted]
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(96)00386-2