ORGN 86 |
Asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines
| Kevin Belyk, Charlotte Beguin, Michael Palucki, Minal Patel, Jimmy O. Dasilva, David Askin, and Nobuyoshi Yasuda. Department of Process Research, Merck Research Laboratories, P.O.Box 2000, Mail Code RY800-C362, Rahway, NJ 07065-0900 |
| Substituted pyrrolidines are structural motifs found in numerous natural products and biologically active compounds. This substitution pattern is prevalent in a series of recently reported pyrrolidine based monoamine transporter inhibitors, coagulation factor Xa inhibitors, endothelin receptor antagonists, and CCR5 antagonists. We have developed a rapid asymmetric synthesis of these chiral pyrrolidines from readily available starting materials. A chiral auxiliary based route and an asymmetric catalytic route were investigated. From these studies, a highly selective two step process was identified, which provides the desired product in up to 95% ee. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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