Synthesis 2017; 49(06): 1410-1418
DOI: 10.1055/s-0036-1588911
paper
© Georg Thieme Verlag Stuttgart · New York

Application of Unusual Grignard Reaction for the Stereoselective Synthesis of Antidepressant Drug (R)-(–)-Venlafaxine

Subhash P. Chavan*
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India   Email: sp.chavan@ncl.res.in
,
Harshali S. Khatod
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India   Email: sp.chavan@ncl.res.in
› Author Affiliations
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Publication History

Received: 18 October 2016

Accepted after revision: 20 October 2016

Publication Date:
28 November 2016 (online)


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Abstract

An enantioselective synthesis of antidepressant drug (R)-(–)-venlafaxine is accomplished as an application of recently explored unusual Grignard reaction. An innovative method for the generation of chirality at extremely reactive benzylic center along with determination of absolute stereochemistry has been discussed. The key steps involved in the synthesis include Sharpless asymmetric dihydroxylation for the induction of chirality and an unusual Grignard reaction.

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