Asymmetric sulfur ylide reactions with boranes: scope and limitations, mechanism and understanding

…, X Ginesta, JN Harvey, VK Aggarwal

Index: Fang, Guang Y.; Wallner, Olov A.; Di Blasio, Nadia; Ginesta, Xavier; Harvey, Jeremy N.; Aggarwal, Varinder K. Journal of the American Chemical Society, 2007 , vol. 129, # 47 p. 14632 - 14639

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Citation Number: 41

Abstract

The reactions of aryl-stabilized sulfur ylides with organoboranes has been studied under a variety of conditions. At 5 or-78° C, the reaction with Et3B gave a mixture of the first and second homologation products, but at-100° C, only the first homologation product was obtained even with just 1.1 equiv of Et3B. Under these optimized conditions, the chiral sulfur ylides (derived from camphor sulfonic acid) with different aryl groups were reacted with ...