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Volumn 135, Issue 32, 2013, Pages 11951-11966

Practical and highly selective sulfur ylide-mediated asymmetric epoxidations and aziridinations using a cheap and readily available chiral sulfide: Extensive studies to map out scope, limitations, and rationalization of diastereo- and enantioselectivities

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC EPOXIDATION; DIASTEREO- AND ENANTIOSELECTIVITY; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVITIES; EXPERIMENTAL EVIDENCE; REACTION CONDITIONS; REACTION MECHANISM; UNSATURATED ALDEHYDES;

EID: 84882256472     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja405073w     Document Type: Article
Times cited : (101)

References (159)
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    • A report on using "chiral micelles" in sulfur ylide asymmetric epoxidations was later shown to be incorrect: Kavanagh, S. A.; Connon, S. J. Tetrahedron: Asymmetry 2008, 19, 1414-1417
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    • The proposed regiochemistry is consistent with literature precedent (e.g., radical addition of mercaptoacetic acid to limonene was reported to give 2:1 adducts, with sulfur forming bonds to the less-substituted carbons of the alkenes). See: Buess, C. M.; Yiannios, C. N.; Fitzgerald, W. T. J. Org. Chem. 1957, 22, 197-200
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