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Tetrasubstituted C ‐Glycosylidenes and C ‐Glycosyl Compounds from Di‐ and Monobromo‐Substituted exo ‐Glycals
Author(s) -
Thien HoangTrang Tran,
Novoa Alexandre,
PellegriniMoïse Nadia,
Chrétien Françoise,
Didierjean Claude,
Chapleur Yves
Publication year - 2011
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.201100949
Subject(s) - chemistry , glycosyl , stereoselectivity , halogenation , palladium , stereochemistry , double bond , organic chemistry , catalysis
Efficient methods for functionalization of readily available exo ‐glycals have been developed. Sequential palladium‐catalysed cross‐coupling of dibromo‐substituted exo ‐glycals was first explored and allowed the formation of new disubstituted exo ‐glycals as single stereoisomers. Bromination of furano‐ and pyrano‐methoxycarbonyl‐ exo ‐glycals led to a new series of monobrominated derivatives. These vinylic bromides were used in carbon‐carbon bond formation through palladium‐catalysed reactions, leading to a new series of previously unknown exo ‐glycals. Further chemical manipulation of the methoxycarbonyl functionalities and stereoselective hydrogenation of the exocyclic double bond led to C ‐glycosyl compounds with high stereocontrol.