33580-05-1Relevant articles and documents
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Minter,D.E.,Fonken,G.J.
, p. 4149 - 4152 (1977)
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The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes
Binns, Falmai,Hayes, Roy,Hodgetts, Kevin J.,Saengchantara, Suthiweth T.,Wallace, Timothy W.,Wallis, Christopher J.
, p. 3631 - 3658 (2007/10/03)
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 in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.
3-Oxiranylprop-2-enals as Synthetic Building Blocks. Easy and Stereoselective Synthesis of Naturally Occurring (E,Z)-1,3,5-Trienes and (E,Z)-2,4-Dienals, Pheromones and Flavour Components
Goldbach, Michael,Jaekel, Edgar,Schneider, Manfred P.
, p. 1434 - 1435 (2007/10/02)
Witting reactions of the title compound (3) lead in one step to the (E,Z)-alkadienyloxiranes (6) and (7), useful starting materials for the preparation of pheromones and flavour components.
