Journal
ORGANIC LETTERS
Volume 12, Issue 9, Pages 2120-2122Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100615j
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Funding
- NIH [CA 93547]
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An efficient and enantiocontrolled three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters is reported. Enantioenriched alpha-selenyl aldehydes, prepared in one step by asymmetric, organocatalytic alpha-selenylation of aldehydes, were directly subjected to a Wittig reaction followed by allylic selenide to selenoxide oxidation and final spontaneous [2,3]-sigmatropic rearrangement to yield the target compounds in 43-65% overall yield and in 94-97% ee.
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