Synlett 2023; 34(12): 1472-1476
DOI: 10.1055/a-2072-4537
cluster
Special Issue Honoring Masahiro Murakami’s Contributions to Science

Regiodivergent Synthesis of Oxadiazocines via Dirhodium-Catalyzed Reactivity of Oxazolidines and α-Imino Carbenes

Olivier Viudes
a   Department of Organic Chemistry, University of Geneva, Quai E. Ansermet 30, 1211 Geneva 4, Switzerland
,
Alejandro Guarnieri-Ibáñez
a   Department of Organic Chemistry, University of Geneva, Quai E. Ansermet 30, 1211 Geneva 4, Switzerland
,
Céline Besnard
b   Laboratory of Crystallography, University of Geneva, Quai E. Ansermet 24, 1211 Geneva 4, Switzerland
,
a   Department of Organic Chemistry, University of Geneva, Quai E. Ansermet 30, 1211 Geneva 4, Switzerland
› Author Affiliations
We thank the Université de Genève and the Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung for financial support (JL: 200020-184843 and 200020-207539).


Dedicated to Prof. Masahiro Murakami on the occasion of his 65th birthday

Abstract

Using electron-rich or electron-poor N-substituted oxazolidines as substrates, selective formation of either ammonium or oxonium ylides is possible in the presence of α-imino carbenes. As such, treatment of 5-membered oxazolidine precursors with N-sulfonyl-1,2,3-triazoles under dirhodium catalysis (2 mol%) affords the regiodivergent synthesis of either 8-membered 1,3,6- or 1,4,6-oxadiazocines upon the initial N or O reactivity with the carbene.

Supporting Information

Primary Data



Publication History

Received: 24 February 2023

Accepted after revision: 12 April 2023

Accepted Manuscript online:
12 April 2023

Article published online:
31 May 2023

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