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Construction of Contiguous Tetrasubstituted Carbon Stereocenters by Intramolecular Crossed Benzoin Reactions Catalyzed by N‐Heterocyclic Carbene (NHC) Organocatalyst

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Abstract:

Abstract

Bicyclic compounds with two contiguous tetrasubstituted carbon stereocenters at bridgehead positions were synthesized by N‐heterocyclic carbene (NHC)‐catalyzed intramolecular crossed benzoin reactions of symmetrical compounds. This desymmetrization strategy was applied to asymmetric synthesis with chiral NHC organocatalysts. Transition‐state models were proposed to explain the enantioselectivity. A tricyclic compound with three contiguous tetrasubstituted carbon stereocenters was synthesized by a stepwise strategy. The molecular structure and absolute configuration of the (+)‐enantiomer of this tricyclic compound were determined by X‐ray crystallographic analysis.

Document Type: Research Article

DOI: http://dx.doi.org/10.1002/adsc.201200499

Affiliations: Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan, phone: (+81)-86-251-8091, Fax: (+81)-86-251-8092

Publication date: November 26, 2012

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