Synlett 2020; 31(09): 899-902
DOI: 10.1055/s-0039-1690856
letter
© Georg Thieme Verlag Stuttgart · New York

O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups

Tomoyuki Suzuki
,
Kosaku Tanaka III
,
Yoshimitsu Hashimoto
,
Nobuyoshi Morita
,
Osamu Tamura
This work was supported by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Number 17K0821 to O.T.).
Further Information

Publication History

Received: 09 January 2020

Accepted after revision: 26 February 2020

Publication Date:
13 March 2020 (online)


Abstract

Amino groups are selectively protected in good yields by reaction with O-alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.

Supporting Information