Synlett 2021; 32(19): 1957-1962
DOI: 10.1055/a-1623-1490
letter

A Rh(II)- or Ag(I)-Catalyzed Formal C–O Bond Insertion of Cyclic Hemiaminal with Aryl Diazoacetate

Cong Xu
,
,
Xiongda Xie
,
Lin Deng
,
Xinfang Xu
,
Albert S. C. Chan
,
Wenhao Hu
Support for this research from the National Natural Science Foundation of China (21971262, 92056201), Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery (2019B030301005), and The Program for Guangdong Introducing Innovative and Entrepreneurial Teams (No. 2016ZT06Y337) is greatly acknowledged.


Abstract

A mild and facile synthetic method via convergent assembly of two reactive intermediates generated in situ has been developed. This method provides an efficient way to construct six- and seven-membered N-heterocycles containing a biaryl linkage. This reaction features a gem-difunctionalization process of diazo compounds with cyclic hemiaminals, delivering α-hydroxyl-β-amino ester derivatives with a tertiary carbon center through a formal C–O bond-insertion transformation.

Supporting Information



Publikationsverlauf

Eingereicht: 10. August 2021

Angenommen nach Revision: 30. August 2021

Accepted Manuscript online:
30. August 2021

Artikel online veröffentlicht:
14. September 2021

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