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Synthesis of novel C 2 ‐symmetrical chiral sulfides and their utility in asymmetric epoxidation of aldehydes
Author(s) -
Ishizaki Miyuki,
Hoshino Osamu
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10204
Subject(s) - chemistry , sulfide , chirality (physics) , bromide , tartaric acid , enantioselective synthesis , silyl ether , ether , benzyl bromide , diol , organic chemistry , silylation , medicinal chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , citric acid , quark
Novel C 2 ‐symmetrical chiral sulfides were synthesized from ( R,R )‐tartaric acid and their utility in the asymmetric epoxidation of aldehydes with benzyl bromide was examined. Among the sulfides used, silyl ether‐type sulfides were found to be superior to diol‐ and benzyl ether‐type sulfides. Also, the presence of an aromatic group on the sulfide was proven to be an important factor for increasing enantioselectivity. Chirality 15:300–305, 2003. © 2003 Wiley‐Liss, Inc.