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A Hetero‐Diels−Alder Approach to Phosphonothiashikimic Acid and New Thiaglycosides
Author(s) -
Heras Montserrat,
Gulea Mihaela,
Masson Serge,
Philouze Christian
Publication year - 2004
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.200300334
Subject(s) - chemistry , lewis acids and bases , dihydroxylation , selectivity , diels–alder reaction , organic chemistry , lewis acid catalysis , shikimic acid , thio , catalysis , acid catalysis , enantioselective synthesis
Phosphonodithioformates undergo hetero‐Diels − Alder cycloadditions with a variety of dienes. In some cases, Lewis acid catalysts were used to control the rate and selectivity of the reactions. Selective radical desulfanylation and subsequent dihydroxylation of the cycloadducts allowed the syntheses of new thiapyran derivatives and, in particular, a phosphono and thio analogue of shikimic acid. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)