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
Full Text: HTML
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 ...
Related Articles:
Highly stereocontrolled synthesis of (2e, 4z)-dienic esters by alumina catalyst
[Tsuboi, Sadao; Masuda, Toshihide; Makino, Hiroshi; Takeda, Akira Tetrahedron Letters, 1982 , vol. 23, # 2 p. 209 - 212]
[Goldbach, Michael; Jaekel, Edgar; Schneider, Manfred P. Journal of the Chemical Society, Chemical Communications, 1987 , # 19 p. 1434 - 1435]