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Synfacts 2005(1): 0107-0107  
DOI: 10.1055/s-2005-872202
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Pyrrolidine Synthesis

Contributor(s): Victor Snieckus, Farhad Nowrouzi
J. Y. L. Chung*, R. Cvetovich, J. Amato, J. C. McWilliams, R. Reamer, L. DiMichele
Merck Research Laboratories, New Jersey, USA
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Publikationsdatum:
21. September 2005 (online)

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Significance

The five-step, chromatography-free asymmetric synthesis of 3 from 1 in 71% overall yield is reported. Starting from one stereogenic center, which was induced by CBS reduction in >98% ee, the pyrrolidine ring was formed with complete inversion at the C-4 center. Following trans/cis epimerization-saponification afforded the pure trans-pyrrolidine carboxylic acid 3 in >99.6% chemical and optical purity. This synthesis was also shown to be applicable to aryl substrates with electronically neutral and rich substituents.