Tetrahedron

The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes

F Binns, R Hayes, KJ Hodgetts, ST Saengchantara…

Index: Binns, Falmai; Hayes, Roy; Hodgetts, Kevin J.; Saengchantara, Suthiweth T.; Wallace, Timothy W.; Wallis, Christopher J. Tetrahedron, 1996 ,  vol. 52,  # 10  p. 3631 - 3658

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Citation Number: 39

Abstract

Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z, 4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1, 2-dimethanol 1 into a variety of naturally occurring 1, 3, 5- alkatrienes and 2, 4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo [3.2. 0] hept-6-en-2-one 4, for use ...