Dynamic kinetic and kinetic resolution of N-Boc-2-lithiopiperidine

…, JJ Patel, S Raimbault, DTE Whittaker

Index: Coldham, Iain; Patel, Jignesh J.; Raimbault, Sophie; Whittaker, David T. E. Chemical Communications, 2007 , # 43 p. 4534 - 4536

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Citation Number: 6

Abstract

The formation and reaction of chiral organolithiums provides a valuable and stereoselective method for asymmetric synthesis . 1 Excellent selectivities have been achieved for the asymmetric deprotonation of a variety of substrates, an important example being N-(tert-butoxycarbonyl)pyrrolidine (N-Boc-pyrrolidine), in which the pro-S hydrogen atom at C-2 is removed with almost complete selectivity using sec-butyllithium and (–)-sparteine as the chiral base. 2 However, ...