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Stereocontrolled rearrangement of silylated vinyloxiranes into α-trialkylsilyl-β,γ-unsaturated aldehydes

✍ Scribed by Christine Courillon; Rachel Le Fol; Estelle Vandendris; Max Malacria

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 165 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01207-0

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✦ Synopsis

Silylated vinyloxiranes 1, substituted on the double bond, have been synthesized and reacted under very mild conditions in the presence of a catalytic amount of palladium (0). They rearrange into txsilylated-13,7-unsaturated aldehydes 2, not only with complete chirality transfer but also with total retention of the double bond stereochemistry.

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