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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.45B [2006] >
IJC-B Vol.45B(11) [November 2006] >
| 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) |
| Source: | IJC-B Vol.45B(11) [November 2006]
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