Journal
SYNTHESIS-STUTTGART
Volume 45, Issue 13, Pages 1886-1898Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1338865
Keywords
chirality; halogenations; alkenes; enantioselectivity; hydroxylations
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Funding
- Columbia University
- NSF [CHE-0844593]
- Ludwig-Maximilians-University-Munich
- ACS Petroleum Research Fund [47481-G]
- Camille and Henry Dreyfus Foundation
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While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.
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