Synlett 2016; 27(02): 215-220
DOI: 10.1055/s-0035-1560802
letter
© Georg Thieme Verlag Stuttgart · New York

Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal

Saikat Chaudhuri
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462 066, Madhya Pradesh, India   Email: alakesh@iiserb.ac.in
,
Amarchand Parida
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462 066, Madhya Pradesh, India   Email: alakesh@iiserb.ac.in
,
Santanu Ghosh
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462 066, Madhya Pradesh, India   Email: alakesh@iiserb.ac.in
,
Alakesh Bisai*
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462 066, Madhya Pradesh, India   Email: alakesh@iiserb.ac.in
› Author Affiliations
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Publication History

Received: 08 July 2015

Accepted after revision: 23 September 2015

Publication Date:
09 November 2015 (online)


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Abstract

A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

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