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Stereoselective [2,3]-sigmatropic rearrangements of unstabilized nitrogen ylides.

ABSTRACT: The steric course of the [2,3]-rearrangement of several unstabilized nitrogen ylides has been investigated. The reactions proceed cleanly through an anti transition state, affording modest to good yields of a single diastereomer of the product. In two examples containing an N-cinnamyl group, a competing [1,2]-rearrangement affords a minor product.

SUBMITTER: Gawley RE

PROVIDER: S-EPMC2518686 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature

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Stereoselective [2,3]-sigmatropic rearrangements of unstabilized nitrogen ylides.

Gawley Robert E RE Moon Kwangyul K

Organic letters 20070712 16

The steric course of the [2,3]-rearrangement of several unstabilized nitrogen ylides has been investigated. The reactions proceed cleanly through an anti transition state, affording modest to good yields of a single diastereomer of the product. In two examples containing an N-cinnamyl group, a competing [1,2]-rearrangement affords a minor product. ...[more]

PMID: 17628071

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