Synthesis of enantiomerically pure (2R, 5R) disubstituted pyrrolidines from D-mannitol

✍ Scribed by M. Marzi; P. Minetti; D. Misiti

• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 515 KB
• Volume: 48
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89042-6

✦ Synopsis

Pyrrolidines 1 and 2 are obtained from D-Mannitol, giving good total yields and in an enantiomerically pure form. Some commentS and studies regarding pyrrolidine ring closure (key step) are also qorted.

Over the last few years, interest in pyrrolidine-type derivatives has grown considerably, from both a synthetic and pharmacological 1 point of view. Quite recently several syntheses of such compounds, destined for use as chiral auxiliaries, have been described 2. However, only a few examples of asymmetric synthesis of trans-2,5_disubstituted py-rrolidines have been reported 3. We have therefore developed a process for the simple, concise asymmetric synthesis of trans-(2R, SR)-bis(benzyloxymethyl)-N-benzyl-pyrrolne