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:

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

Communication | Special issue | Vol 66, No. 1, 2005, pp.75-80
Published online, 21st October, 2005
DOI: 10.3987/COM-05-S(K)24
A Cation-Exchange Resin Promoted Imino Aldol Reaction of Chiral Alkoxyketene Silyl Acetals with α,β-Unsaturated Imines, Leading to a Facile Synthesis of β-Lactams

Makoto Shimizu,* Masanori Tachi, Shiho Fukukshima, and Iwao Hachiya

*Department of Chemistry for Materials, Faculty of Engineering, Mie University, 1515 Uehama-cho, Tsu, Mie 514-5807, Japan


Imino aldol reaction of chiral ketene silyl acetals derived from 3-hydroxybutanoates with α,β-unsaturated imines proceeds smoothly to give β-amino esters in good yields with high syn-selectivity under the influence of a cation-exchange resin. Subsequent treatment with tert-butylmagnesium chloride gave β-lactams in a highly stereoselective manner.