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Synlett 2015; 26(03): 375-379
DOI: 10.1055/s-0034-1379506
letter
© Georg Thieme Verlag Stuttgart · New York

A New Approach to the Synthesis of 4-Phosphonylated β-Lactams

Dorota G. Piotrowska*
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Łódź, Poland   Email: dorota.piotrowska@umed.lodz.pl   Email: iwona.glowacka@umed.lodz.pl
,
Aneta Bujnowicz
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Łódź, Poland   Email: dorota.piotrowska@umed.lodz.pl   Email: iwona.glowacka@umed.lodz.pl
,
Andrzej E. Wróblewski
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Łódź, Poland   Email: dorota.piotrowska@umed.lodz.pl   Email: iwona.glowacka@umed.lodz.pl
,
Iwona E. Głowacka*
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Łódź, Poland   Email: dorota.piotrowska@umed.lodz.pl   Email: iwona.glowacka@umed.lodz.pl
› Author Affiliations
Further Information

Publication History

Received: 10 September 2014

Accepted after revision: 03 November 2014

Publication Date:
07 January 2015 (online)

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Abstract

The general and efficient method for the synthesis of 4-phosphonylated β-lactams from N-methyl-C-(diethoxyphosphonyl)nitrone and selected terminal alkynes via Kinugasa reaction was reported. Application of microwave irradiation significantly shortened the reaction time. Stereochemistry of diastereoisomeric products was established based on vicinal H3–H4 couplings in the β-lactam ring.

Key words

Kinugasa reaction - β-lactams - phosphonate - diastereoselectivity - relative configuration - microwave irradiation.
 

  • References and Notes

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