Synthesis 2020; 52(12): 1823-1832
DOI: 10.1055/s-0039-1690864
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of α-Halo β-Amino Acid Derivatives via the Difunctional Coupling of Ethyl α-Diazoacetate with Silyl Halides and N,O-Acetals or Aromatic Tertiary Amines

Norio Sakai
,
Kazuki Sasaki
,
Hiroki Suzuki
,
Further Information

Publication History

Received: 10 February 2020

Accepted after revision: 05 March 2020

Publication Date:
23 March 2020 (online)


Abstract

The difunctionalization of ethyl α-diazoacetate (EDA) using silyl halides as a nucleophile and N,O-acetals as an electrophile under metal-free conditions is described. This process undergoes a novel three-component coupling (3-CC) reaction using EDA, which leads to a one-pot preparation of α-halo β-amino acid esters. Also, this protocol could be adapted to accept an electrophile composed of aromatic tertiary amines. In both 3-CC reactions, the key reaction intermediate is an iminium intermediate that can be easily and effectively generated either from N,O-acetals or from aromatic tertiary amines.

Supporting Information

 
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