Synlett 2021; 32(10): 1024-1028
DOI: 10.1055/s-0037-1610773
letter

Direct Synthesis of N-Protected Serine- and Threonine-Derived Weinreb Amides via Diboronic Acid Anhydride-Catalyzed Dehydrative Amidation: Application to the Concise Synthesis of ­Garner’s Aldehyde

,
Naoki Ohse
,
Naoya Takahashi
,
Sari Urata
,
Masayoshi Koshizuka
,

JSPS KAKENHI Grant Number 19K07000 to N.S. for Scientific Research (C).


Preview

Abstract

An efficient method for the direct synthesis of Weinreb amides derived from serine and threonine derivatives via diboronic acid anhydride-catalyzed hydroxy-directed amidation is described. This is the first successful example of the synthesis of serine- or threonine-derived Weinreb amides using catalytic dehydrative amidations. The methodology could be applied to the concise synthesis of Garner’s aldehyde.

Supporting Information



Publication History

Received: 22 March 2021

Accepted after revision: 10 April 2021

Article published online:
04 May 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany