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Stereocontrolled reactions induced by a thermolabile group. Synthesis of optically active 1,3-diols.

✍ Scribed by Robert Bloch; Michel Bortolussi; Christian Girard; Matar Seck

Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 684 KB
Volume: 48
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89007-4

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✦ Synopsis

Wittig Homer-Michael reactions of phosphonates with optically active lactol 1 lead prefetentially to one diastereoisomer 2. Force field calculations conducted on one pair of diastereoisomers 2c and 2'c predict that these isomers must exist in different conformations of similar energies. IH NMR data are in good agreement with these predictions. The dihydrofurans obtained by retro Diels-Alder reactions of 2 are easily transformed into optically pure 1,3diols, precursors of R-(+)-a-lipoic acid and (-)-(lR,3R,5S)-1,fdtmethyl -2,9dioxabicyclo [3.3.l]nonane.

During our investigations directed at the steric control of a variety of reactions by a thermolabile group, we have shown that tricyclic ethers 2. precursors of optically active dihydrofurans 3 can be highly selectively obtained from &ii, non racemic lactol 1 by a tandem Wittig Homer-Michael reaction followed by a retro Diels-Alder cleavage 1.

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