Journal
ORGANIC LETTERS
Volume 11, Issue 2, Pages 409-412Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8027225
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Funding
- National Institutes of Health [CA 22215]
- Eisai Research Institute
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With focus on the steric effects present in the transition states for the [3,3]-sigmatropic rearrangement, the substrate 5 has been designed to improve the overall stereoselectivity of the Ireland-Claisen rearrangement. Experimentally, it has been found that (1) only Z-6 rearranges to 7 at 80 degrees C and (2) E-6 isomerizes to Z-6 at 80 degrees C, thereby allowing the transformation of 5 into 7 in an almost quantitative yield. To illustrate the usefulness of this approach, two additional examples are given.
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