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RESEARCH ARTICLE
Contents Vol 62(8)

Stereoselective Nucleophilic Addition of Potassium Alkyltrifluoroborates to Cyclic N-Acyliminium Ions: a Simple and Mild Approach to Chiral 5-Alkyl-pyrrolidin-2-ones

Adriano S. Vieira A , Fernando P. Ferreira B , Alexandre S. Guarezemini C and Helio A. Stefani A B C D
+ Author Affiliations
- Author Affiliations

A Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, Brazil.

B Deparmento de Biofísica, Universidade Federal de São Paulo, São Paulo, Brazil.

C Instituto de Química, Universidade de São Paulo, São Paulo, Brazil.

D Corresponding author. Email: hstefani@usp.br

Australian Journal of Chemistry 62(8) 909-916 https://doi.org/10.1071/CH09067
Submitted: 3 February 2009  Accepted: 8 April 2009   Published: 13 August 2009

Abstract

The stereoselective nucleophilic addition of potassium alkyltrifluoroborates to cyclic N-acyliminium ions derived from N-benzyl-3,4,5-triacetoxy-pyrrolidin-2-one, which affords 5-substituted-pyrrolidin-2-ones, is described. The products are obtained in moderate to good yields and are produced predominantly as the anti diastereomer.


Acknowledgements

The authors acknowledge Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) for financial support. H.A.S. thanks FAPESP for grant number 07/59404-2, while A.S.V. thanks FAPESP for a fellowship (06/50190-7).


References


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* The compound (3R,4R)-3,4-diacetoxy-1,5-diallyl-pyrrolidin-2-one[3e] gives the following spectroscopic data: Anti isomer: H-5 δ 3.99 (ddd, J 9.8, 8.0, 4.4); Syn isomer: H-5 δ 3.60 (ddd, J 8.5, 5.0, 3.4). The compound (3R,4R)-3,4-diacetoxy-5-allyl-1-benzyl-pyrrolidin-2-one (3f, this work) gives the following spectroscopic data: Anti isomer: H-5 δ 4.11 (ddd, J 8.1, 6.5, 6.5); Syn isomer: H-5 δ 4.05 (ddd, J 6.5, 6.5, 4.6).