Journal
ORGANIC LETTERS
Volume 19, Issue 3, Pages 552-555Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03719
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Funding
- NSERC (Canada)
- University of Alberta for a Queen Elizabeth II graduate scholarship
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A novel approach to medium-sized cyclic ethers was devised using a Stevens [1,2]-shift of a sulfonium ylide derived from a readily accessible six-membered mixed-monothioacetal precursor. The concise and efficient transformation offers a surprising degree of chirality transfer with observed retention of stereochemical configuration on the anomeric migrating carbon and has been applied as the key step in an enantioselective formal synthesis of (+)-laurencin.
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