Synlett 2021; 32(05): 521-524
DOI: 10.1055/s-0040-1707161
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The Power of Transition Metals: An Unending Well-Spring of New Reactivity
© Georg Thieme Verlag Stuttgart · New York

Zinc-Catalyzed Transacetalization of N,O-Acetals into N,N-Acetals with Benzotriazoles, Indazoles, and Azides

Authors

  • Sang Ik Shin

  • Nguyen H. Nguyen

  • Jangbin Im

  • Seunghoon Shin

    Department of Chemistry, Center for New Directions in Organic Synthesis (CNOS) and Research Institute for Natural Sciences, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Korea   eMail: sshin@hanyang.ac.kr

This work was supported by the National Research Foundation of Korea (Grant Numbers NRF-2012M3A7B4049653, NRF-2014–011165, and NRF-2017R1A2B4010888).
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Publikationsverlauf

Received: 02. Mai 2020

Accepted after revision: 31. Mai 2020

Publikationsdatum:
23. Juni 2020 (online)


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This paper is dedicated to Professor Barry M. Trost to celebrate his career on the occasion of 20 years of Science of Synthesis.

Abstract

N,O-Acetals obtained from β-oxidation of ynamides underwent transacetalization with benzotriazoles, leading to N,N-acetals. The Zn(OTf)2 efficiently catalyzed the process, and the reaction is further accelerated in hexafluoroisopropanol, providing a single N1-regiosiomer. The transacetalization conditions developed could be extended to other N-donors, such as 1H-indazole and TMSN3 to afford the corresponding N,N-acetals.

Supporting Information