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Synthesis and Use of Achiral Oxazolidine‐2‐thiones in Selective Preparation of trans 2,5‐Disubstituted Tetrahydrofurans
Author(s) -
Jalce Gaël,
Franck Xavier,
Figadère Bruno
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800907
Subject(s) - chemistry , lactol , oxazolidine , steric effects , glycosylation , stereochemistry , organic chemistry , lactone , biochemistry
The use of achiral N ‐acetyloxazolidine‐2‐thiones in the C ‐glycosylation of lactol acetates has allowed us to prepare with high diastereoselectivity the expected trans 2,5‐disubstituted tetrahydrofurans. A study based on the role of the steric hindrance of the N ‐acetyloxazolidine‐2‐thiones is reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)