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Stereoselective synthesis of (z)- and (e)-1,3-alkadienes from aldehydes using organotitanium and lithium reagents

✍ Scribed by Yoshihiko Ikeda; Junzo Ukai; Nobuo Ikeda; Hisashi Yamamoto

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 656 KB
Volume: 43
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)90006-7

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✦ Synopsis

3-(Diphenylphosphinojalfylltftanium reagent qenerated easily from allyldiphenylphosphine

condenses with aldehydes to give (Z)-1,3-alkadienes in a highly reqio-and stereoselective manner.

In contrast, lithiated allyldiphenylphosphine oxide condenses with aldehydes to give (El-1,3-alkadienes directly and stereoselectively in good yield.

Similarly, lithiated (1-buten-3-ylldiphenylphosphine oxide condenses with aldehydes to give (El-3-methyl-1,3-alkadienes.

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