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A New Target for Highly Stereoselective Katsuki–Sharpless Epoxidation – One‐Pot Synthesis of C 2 ‐Symmetric 2,2′‐Bioxiranes
Author(s) -
Bilenko Vitaliy,
Jiao Haijun,
Spannenberg Anke,
Fischer Christine,
Reinke Helmut,
Kösters Jutta,
Komarov Igor,
Börner Armin
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600711
Subject(s) - chemistry , epoxide , sharpless epoxidation , stereoselectivity , conjugated system , stereochemistry , absolute configuration , stacking , alcohol , ab initio , enantioselective synthesis , organic chemistry , catalysis , polymer
Abstract The double asymmetric Katsuki–Sharpless epoxidation of a conjugated diallyl alcohol affords excellent enantioselectivity (>97 % ee ), the product being isolated as the stable p ‐nitrobenzoate 5a or tosylate 5b . The optical purities of the chiral epoxides were determined by HPLC on chiral columns, while the molecular structures of compounds 5a and 7 and the absolute configuration of mono‐epoxide 12 were confirmed by X‐ray crystallography. Possible π–π stacking interaction has been evaluated by ab initio calculation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)