CHIRALITY TRANSMISSION VIA TANDEM SIGMATROPIC REARRANGEMENT: REGIO- AND STEREOCHEMICAL OUTCOME IN THE TANDEM WITTIG-OXY-COPE SEQUENCE OF ALLYL cis-5-METHYL-2-CYCLOHEXENYL ETHER

DOI: 10.1016/S0040-4039(00)87746-1

Source and publish data:

Tetrahedron Letters p. 3931 - 3934 (1982)

Update date:2022-08-05

Topics:

Authors:

Sayo, Noboru

Kimura, Yasuhiro

Nakai, Takeshi

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Article abstract of DOI:10.1016/S0040-4039(00)87746-1

The titled sigmatropic sequence proceeds with complete net retention of configuration, and surprisingly, suffers from a regiochemical complication arising mainly from the unexpected competition of the (2,3)- vs. (1,2)-shift in the Wittig process, as revealed by the use of the deuterium-labeled substrate.

Full text of DOI:10.1016/S0040-4039(00)87746-1

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