Copper(I)-catalyzed intramolecular asymmetric [2 + 2] photocycloaddition. Synthesis of both enantiomers of cyclobutane derivatives

Sarkar, Niladri ; Nayek, Abhijit ; Ghosh, Subrata (2004) Copper(I)-catalyzed intramolecular asymmetric [2 + 2] photocycloaddition. Synthesis of both enantiomers of cyclobutane derivatives Organic Letters, 6 (12). pp. 1903-1905. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol049696h

Related URL: http://dx.doi.org/10.1021/ol049696h

Abstract

A simple approach for asymmetric induction in Cu(I)-catalyzed [2+2] photocycloaddition, where asymmetric catalysts or chiral auxiliaries were inefficient, has been developed using the concept of chirality transfer from the readily available 2, 3-di-O-cyclohexylidine-(R)-(+)-glyceraldehyde. An anion-induced cleavage of the tetrahydrofuran ring of the resulting oxa-bicyclo[3.2.0]heptanes led to a convenient access to the synthetically useful cis-1,2-disubstituted cyclobutanes in enantiomerically pure form.

Item Type:Article
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ID Code:12231
Deposited On:10 Nov 2010 04:55
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