Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
1,4-CHIRALITY TRANSFER VIA THE [2,3]-WITTIG REARRANGEMENT OF CHIRAL ALLYLIC PROPARGYL ETHER SYSTEM. A NEW, PRACTICAL ENTRY TO CHIRAL PROPARGYLIC ALCOHOLS
Noboru SayoFumiyuki ShiraiTakeshi Nakai
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JOURNALS FREE ACCESS

1984 Volume 13 Issue 2 Pages 255-258

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Abstract

The [2,3]-Wittig rearrangement of enantiomerically-enriched α-methylallyl propargyl ethers provides a high degree (ca. 90%) of 1,4-chirality transfer, together with 95–98% of (E)-selectivity. The observed sense of 1,4-chirality transfer is discussed on mechanistic grounds.

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