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Stereoselective Dearomatizing Addition of Nucleophiles to Uncomplexed Benzene Rings: A Route to Carbocyclic Sugar Analogues
Author(s) -
Clayden Jonathan,
Parris Sean,
Cabedo Nuria,
Payne Andrew H.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801078
Subject(s) - chemistry , stereoselectivity , reagent , aryl , nucleophile , lithium (medication) , alkyl , stereochemistry , sequence (biology) , sugar , medicinal chemistry , organic chemistry , catalysis , medicine , biochemistry , endocrinology
Versatile synthetic intermediates were formed by the dearomatization of 2‐aryl 4,5‐diphenyloxazolines with secondary alkyl lithium reagents in the presence of N , N ′‐dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups.