Co(III)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone

R. Santhosh Reddy; Pandurang V. Chouthaiwale; Gurunath Suryavanshi; Vilas B. Chavan; Arumugam Sudalai

doi:10.1039/C0CC00650E

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Co(iii)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone†

R. Santhosh Reddy,^a Pandurang V. Chouthaiwale,^a Gurunath Suryavanshi,^a Vilas B. Chavan^a and Arumugam Sudalai*^a

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* Corresponding authors

^a Chemical Engineering and Process Development Division, National Chemical Laboratoty, Pashan Road, Pune, India
E-mail: a.sudalai@ncl.res.in
Fax: +91-02025902675

Abstract

The HKR of racemic syn- or anti- alkoxy- and azido epoxides catalyzed by Co(salen) complex affords a practical access to a series of enantioenriched syn- or anti- alkoxy- and azido epoxides and the corresponding 1,2-diols. This strategy has been successfully employed in the concise, enantioselective synthesis of bioactive molecules such as (S,S)-reboxetine and (+)-epi-cytoxazone.

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Supplementary files

Full experimental procedures, ¹H NMR, and ¹³C NMR, spectra of all new compounds PDF (1282K)

Article information

DOI: https://doi.org/10.1039/C0CC00650E
Article type: Communication
Submitted: 29 Mar 2010
Accepted: 05 May 2010
First published: 04 Jun 2010

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Chem. Commun., 2010,46, 5012-5014

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Co(III)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone

R. S. Reddy, P. V. Chouthaiwale, G. Suryavanshi, V. B. Chavan and A. Sudalai, Chem. Commun., 2010, 46, 5012 DOI: 10.1039/C0CC00650E

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Chemical Communications

Co(iii)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone†

Abstract

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Co(III)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone

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