Asymmetric intramolecular [2+ 2] photocycloadditions: α-and β-hydroxy acids as chiral tether groups

S Faure, S Piva-Le-Blanc, C Bertrand…

Index: Faure, Sophie; Piva-Le-Blanc, Sylvie; Bertrand, Cyrille; Pete, Jean-Pierre; Faure, Rene; Piva, Olivier Journal of Organic Chemistry, 2002 , vol. 67, # 4 p. 1061 - 1070

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Citation Number: 42

Abstract

Chiral α-and β-hydroxy acids such as (S)-lactic acid,(S)-phenyllactic acid,(S)-mandelic acid, or (3 R)-3-hydroxybutyric acid have been used as tether groups for intramolecular and diastereoselective [2+ 2] photocycloaddition of 3-oxocyclohexene carboxylic acid derivatives. Total regiocontrol toward the straight adduct and high diastereoselectivities (up to 94%) were observed in the case of butenyl lactate 11. After separation of the two ...