Synthesis of Enantiopure 3-Azabicyclo[3.2.0]heptanes by Diastereoselective Intramolecular [2+2] Photocycloaddition Reactions on Chiral Perhydro-1,3-benzoxazines
- 21 May 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (12) , 4923-4931
- https://doi.org/10.1021/jo034251c
Abstract
[2+2] photocycloadditions involving chiral 3-acryloyl-2-vinylperhydro-1,3-benzoxazines derived from (−)-8-aminomenthol are highly diastereoselective reactions. The facial selectivity depends on the type of substitution at the vinyl double bond, and always leads to cis-fused bicyclic derivatives. The de is good for compounds with one substituent at the outer carbon of the double bond at C-2, but only one diastereomer is formed in cyclizations of compounds with two substituents at that position. The elimination of the menthol appendage gives enantiopure 3-azabicyclo[3.2.0]heptanes.Keywords
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