Issue 36, 2013

Regioselective monochloro substitution in carbohydrates and non-sugar alcoholsviaMitsunobu reaction: applications in the synthesis of reboxetine

Abstract

A regioselective high yielding monochloro substitution (chlorohydrin formation) via Mitsunobu reaction is reported. In carbohydrates and sterically hindered non-sugars, only the primary hydroxyl group is chlorinated, whereas in the non-sugar 1,2- and 1,3-alcohols, predominantly the secondary chloride substitution occurs. The versatile methodology provides indirect access to epoxides with the retention of configuration, as against conventional Mitsunobu reaction which generates epoxides with inversion. The methodology was successfully used as a key step in the synthesis of optically active diastereoisomers of the antidepressant drug reboxetine from (R)-2,3-O-cyclohexylidene-D-glyceraldehyde in ∼43% overall yields.

Graphical abstract: Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: applications in the synthesis of reboxetine

Supplementary files

Article information

Article type
Paper
Submitted
25 Apr 2013
Accepted
18 Jul 2013
First published
23 Jul 2013

Org. Biomol. Chem., 2013,11, 6195-6207

Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: applications in the synthesis of reboxetine

A. R. Dar, M. A. Aga, B. Kumar, S. K. Yousuf and S. C. Taneja, Org. Biomol. Chem., 2013, 11, 6195 DOI: 10.1039/C3OB40853A

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