Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives

The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydrox...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-10, Vol.68 (20), p.7779-7787
Main Authors: Carreño, M. Carmen, Des Mazery, Renaud, Urbano, Antonio, Colobert, Françoise, Solladié, Guy
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (−)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034817x