Asymmetric Substitutions of 2??Lithiated N??Boc??piperidine and N??Boc??azepine by Dynamic Resolution

I Coldham, S Raimbault, DTE Whittaker…

文献索引：Coldham, Iain; Raimbault, Sophie; Whittaker, David T. E.; Chovatia, Praful T.; Leonori, Daniele; Patel, Jignesh J.; Sheikh, Nadeem S. Chemistry - A European Journal, 2010 , vol. 16, # 13 p. 4082 - 4090

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被引用次数: 38

摘要

Abstract Proton abstraction of N-tert-butoxycarbonyl-piperidine (N-Boc-piperidine) with sBuLi and TMEDA provides a racemic organolithium that can be resolved using a chiral ligand. The enantiomeric organolithiums can interconvert so that a dynamic resolution occurs. Two mechanisms for promoting enantioselectivity in the products are possible. Slow addition of an electrophile such as trimethylsilyl chloride allows dynamic resolution under ...