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ChemInform Abstract: The Synthesis of Alkenes via epi-Phosphonium Species. Part 1. An anti-Wittig Elimination.

✍ Scribed by Nicholas J. Lawrence; Faiz Muhammad

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

The Synthesis of Alkenes via epi-Phosphonium Species. Part 1. An anti-Wittig Elimination.

-Phosphinyl alcohols (II) and (V), prepared by the reduction of syn-and anti-phosphinoyl alcohols (I) and (IV), give upon treatment with PCl 3 and Et 3 N (Z)-and (E)-alkenes, correspondingly, by anti-elimination reactions. An attempted synthesis of antimitotic agent (Z)-combretastatin from syn-isomer (VII) fails. Instead of the expected corresponding syn-phosphinyl alcohol, the (E)-elimination product (VIII) is obtained. An alternative synthesis of 1,2-phosphinyl alcohols from the corresponding phosphine-borane complexes is demonstrated for syn alcohol (XIV) which gives the expected alkene (XV) with a marked lack of stereospecificity. -

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