Enantiospecific photochemical Norrish/Yang type II reaction of nonbiaryl atropchiral α-oxoamides in solution—axial to point chirality transfer

…, N Barooah, A Ugrinov, J Sivaguru

Index: Ayitou, Anoklase Jean-Luc; Jesuraj, Josepha L.; Barooah, Nilotpal; Ugrinov, Angel; Sivaguru Journal of the American Chemical Society, 2009 , vol. 131, # 32 p. 11314 - 11315

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Citation Number: 47

Abstract

α-Oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers. These axially chiral α-oxoamides undergo enantiospecific photochemical γ-Hydrogen abstraction in CHCl3 to yield β-lactams with high enantioselectivity (er∼ 90: 10) in solution. The extent of enantioselectivity was found to be dependent on the reaction temperature.

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