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Updated: Jul 13, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereoselective [2,3]-sigmatropic rearrangements of unstabilized nitrogen ylides
Robert E Gawley1, Kwangyul Moon
1Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA. bgawley@uark.edu
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.
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