Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 60, No. 11, 2003, pp.2485-2498
Published online, 16th September, 2003
DOI: 10.3987/COM-03-9854
A Stereoselective Approach to Both 3,4-trans-Disubstituted Pyrrolidin-2-ones and Pyrrolidines. A Convenient Synthesis of (3R,4R)-4-Benzyl-3-pyrrolidinecarboxylic Acid

Roberta Galeazzi, Gianluca Martelli, Giovanna Mobbili, Mario Orena,* and Maria Panagiotaki

*Dipartimento di Scienze dei Materiali e della Terra - Università Politecnica delle Marche, Via Brecce Bianche, I-60131 Ancona, Italy

Abstract

Chiral 4-alkyloxymethyl- and silyloxymethylpyrrolidin-2-ones, (10a-c), underwent alkylation to give the corresponding 3,4-trans-disubstituted pyrrolidin-2-ones, (11a-g), in good yield and total stereoselection, as shown by 1H NMR spectral data and n.O.e. experiments. Moreover compounds (11a-c) were converted into the corresponding 3,4-trans-disubstituted pyrrolidines, (12a-c). Removal of the chiral auxiliary from 12a, followed by protection of the nitrogen with t-Boc group, led to the corresponding derivative (13). Cleavage of the benzyl ether and subsequent oxidation of the hydroxy function afforded (3R,4R)-4-benzyl-3-pyrrolidinecarboxylic acid (4).