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Concise Asymmetric Synthesis of (+)-CP-99,994 and (+)-L-733,060 via Efficient Construction of Homochiral syn-1,2-Diamines and syn-1,2-Amino Alcohols

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journal contribution
posted on 18.04.2008, 00:00 by Run-Hua Liu, Kai Fang, Bing Wang, Ming-Hua Xu, Guo-Qiang Lin
An efficient asymmetric synthesis of human NK-1 SP receptor antagonists (+)-CP-99,994 and (+)-L-733,060 was achieved starting from a common chiral intermediate (5). Our route featured the SmI2-induced reductive coupling of N-tert-butanesulfinyl imine (7) with aldehyde (6) as the key step as well as pivotal transformations of the anti-1,2-amino alcohol thus obtained to homochiral syn-1,2-amino alcohol and syn-1,2-diamine for the asymmetric synthesis of 2,3-disubstituted piperidines.