Practical and highly selective sulfur ylide-mediated asymmetric epoxidations and aziridinations using a cheap and readily available chiral sulfide: extensive studies to …

…, M Lusi, EM McGarrigle, VK Aggarwal

Index: Riches, Samantha L.; Saha, Chandreyee; Filgueira, Noelia Fontan; Grange, Emma; McGarrigle, Eoghan M.; Aggarwal, Varinder K. Journal of the American Chemical Society, 2010 , vol. 132, # 22 p. 7626 - 7630

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Citation Number: 23

Abstract

The chiral sulfide, isothiocineole, has been synthesized in one step from elemental sulfur, γ- terpinene, and limonene in 61% yield. A mechanism involving radical intermediates for this reaction is proposed based on experimental evidence. The application of isothiocineole to the asymmetric epoxidation of aldehydes and the aziridination of imines is described. Excellent enantioselectivities and diastereoselectivities have been obtained over a wide ...