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

Dorota G. Piotrowska; Aneta Bujnowicz; Andrzej E. Wróblewski; Iwona E. Głowacka

doi:10.1055/s-0034-1379506

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(03): 375-379
DOI: 10.1055/s-0034-1379506

letter

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

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Abstract

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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.

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Referenzen

References and Notes
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