Tetrahedron: Asymmetry

Application of new chiral auxiliaries, trans-2-(N-arylsulfonyl-N-benzyl) cyclohexanols, in an asymmetric radical cyclization

A Nishida, F Shirato, M Nakagawa

Index: Nishida, Atsushi; Shirato, Fumie; Nakagawa, Masako Tetrahedron Asymmetry, 2000 ,  vol. 11,  # 18  p. 3789 - 3805

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Citation Number: 15

Abstract

There have been important recent advances in radical chemistry, particularly in asymmetric synthesis. 1 We have reported a synthesis of chiral cycloalkenyl acetic acids using diastereoselective radical cyclization with 8-phenylmenthol as the chiral auxiliary (Scheme 1). 2 In this reaction, the presence of a bulky Lewis acid such as methylaluminum bis(2,6-di-t-butyl-4-methylphenoxide ) (MAD) 3 is essential for high selectivity. ... 8-Phenylmenthol is a cyclohexanol-type ...