A New Target for Highly Stereoselective Katsuki–Sharpless Epoxidation – One‐Pot Synthesis of  C  2 ‐Symmetric 2,2′‐Bioxiranes | Zendy

Bilenko Vitaliy | Zendy; Jiao Haijun | Zendy; Spannenberg Anke | Zendy; Fischer Christine | Zendy; Reinke Helmut | Zendy; Kösters Jutta | Zendy; Komarov Igor | Zendy; Börner Armin | Zendy

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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

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)

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