Stereoselective Dearomatizing Addition of Nucleophiles to Uncomplexed Benzene Rings: A Route to Carbocyclic Sugar Analogues | Zendy

Clayden Jonathan | Zendy; Parris Sean | Zendy; Cabedo Nuria | Zendy; Payne Andrew H. | Zendy

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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.

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