Organic letters

Synthesis of planar-chiral paracyclophanes via samarium (II)-catalyzed intramolecular pinacol coupling

T Ueda, N Kanomata, H Machida

Index: Ueda, Tsuyoshi; Kanomata, Nobuhiro; Machida, Hajime Organic Letters, 2005 , vol. 7, # 12 p. 2365 - 2368

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Citation Number: 43

Abstract

A series of [n] paracyclophanediols (n= 8-12) was synthesized by samarium-catalyzed pinacol coupling for their ansa-bridge formation. Enantiomerically pure [n] paracyclophane esters were derived from the diols in a several steps via chiral resolution (for n= 10) or via crystallization-induced asymmetric transformation (for n= 11) by using amino alcohol auxiliaries and their selective cleavages.