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Title: Asymmetric induction in copper (I)-catalyzed intramolecular [2 + 2] photocycloaddition: Synthesis of enantiopure cyclobutane derivatives
Authors: Sarkar, Niladri
Ghosh, Subrata
Keywords: Asymmetric synthesis;catalysis;cyclobutane;ether cleavage;photocycloaddition
Issue Date: Nov-2006
Publisher: CSIR
IPC Code: Int. Cl.8 C07C
Abstract: A simple approach for asymmetric induction in copper (I)-catalyzed intramolecular [2 + 2] photocycloaddition of 1,6-dienes, where asymmetric catalysis or chiral auxiliaries have been inefficient, has been developed using the concept of chirality transfer from the readily available 2,3-di-O-cyclohexylidine–(R)-(+)-glyceraldehyde to produce enantiopure oxa-bicyclo[3.2.0]heptane derivatives. A novel anion-induced cleavage of the tetrahydrofuran ring in these oxa-bicyclo[3.2.0]heptane derivatives has led to a convenient access to the synthetically useful cis-1,2-disubstituted cyclobutanes in enantiomerically pure form.
Page(s): 2474-2484
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(11) [November 2006]

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