Synlett 2016; 27(02): 173-176
DOI: 10.1055/s-0035-1560494
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© Georg Thieme Verlag Stuttgart · New York

Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer

Anon Bunrit
a  Department of Chemistry, BMC, Uppsala University, Box 576, 75123 Uppsala, Sweden
,
Christian Dahlstrand
a  Department of Chemistry, BMC, Uppsala University, Box 576, 75123 Uppsala, Sweden
,
Pemikar Srifa
a  Department of Chemistry, BMC, Uppsala University, Box 576, 75123 Uppsala, Sweden
,
Sandra K. Olsson
a  Department of Chemistry, BMC, Uppsala University, Box 576, 75123 Uppsala, Sweden
,
Genping Huang
b  Department of Organic Chemistry, Stockholm University, 10691 Stockholm, Sweden   Email: joseph.samec@su.se
c  Department of Chemistry, School of Science, Tianjin University, 300072 Tianjin, P. R. of China
,
Srijit Biswas
a  Department of Chemistry, BMC, Uppsala University, Box 576, 75123 Uppsala, Sweden
d  Centre of Biomedical Research, SGPGIMS Campus, Raebareli Road, 226014 Lucknow, India
,
Fahmi Himo
b  Department of Organic Chemistry, Stockholm University, 10691 Stockholm, Sweden   Email: joseph.samec@su.se
,
Joseph S. M. Samec*
a  Department of Chemistry, BMC, Uppsala University, Box 576, 75123 Uppsala, Sweden
b  Department of Organic Chemistry, Stockholm University, 10691 Stockholm, Sweden   Email: joseph.samec@su.se
› Author Affiliations
Further Information

Publication History

Received: 26 August 2015

Accepted after revision: 16 September 2015

Publication Date:
15 October 2015 (online)

Abstract

A brief overview of the development of direct substitution of the hydroxyl (OH) group of alcohols in our research group is presented. By applying a Brønsted acid, an intramolecular substitution of the OH group in stereogenic alcohols with chirality transfer was achieved. Noteworthy, the intramolecular substitution has a wide scope in respect to both the nucleophile and also the nucleofuge. A mechanistic study by both experiments and DFT calculations revealed a unique reaction pathway in which the Brønsted acid operates in a bifunctional manner to promote an SN2-type reaction mechanism.

 
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