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Readily Synthesized Chiral Sulfides as Reagents for Asymmetric Epoxidation
Author(s) -
Badine D. Michael,
Hebach Christina,
Aggarwal Varinder K.
Publication year - 2006
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600079
Subject(s) - ylide , propargyl , aryl , chemistry , alkyl , sulfur , reagent , enantioselective synthesis , organic chemistry , catalysis , combinatorial chemistry
Chiral oxathianes were designed, synthesized, and successfully used for asymmetric sulfur ylide mediated epoxidation. A considerable emphasis has been placed upon the design of sulfides with suitable architecture in a small number of steps (three or four). The use of (4a R ,6 S ,8a R )‐6‐isopropenyl‐8a‐methyloctahydro‐1,4‐benzoxathiane in asymmetric epoxidation resulted in good diastereo‐ and enantioselectivity in the formation of stilbene oxide, and (2 S ,6 S )‐2‐allyl‐2,3,3,6‐tetramethyl‐1,4‐oxathiane produced even better results. Moderate to good diastereoselectivities with essentially complete enantioselectivities were observed in the formation of alkyl–aryl‐, vinyl–aryl‐, and propargyl–aryl‐substituted epoxides. The selectivities were rationalized and supported by density functional theory calculations.