期刊
ORGANIC LETTERS
卷 20, 期 17, 页码 5327-5331出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02248
关键词
-
资金
- NSERC
- McLean Foundation
- Canada Foundation for Innovation [17545, 19119]
- Province of Ontario
A new mode of catalysis of the semipinacol rearrangement of 2,3-epoxy alcohols is described. In combination with a halide salt additive, diarylborinic acids promote a Type II rearrangement that occurs with net retention of configuration. This unusual stereochemical outcome is consistent with a mechanism involving regioselective ring opening of the epoxy alcohol by halide, followed by rearrangement of the resulting halohydrin-derived borinic ester. The protocol is applicable to a range of substrates, enabling ring contractions and expansions as well as stereospecific syntheses of acyclic beta-hydroxycarbonyl compounds.
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