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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*

*Showa Pharmaceutical University, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan, Email: tamuraac.shoyaku.ac.jp

T. Suzuki, K. Tanaka III, Y. Hashimoto, N. Morita, O. Tamura, Synlett, 2020, 31, 899-902.

DOI: 10.1055/s-0039-1690856 (free Supporting Information)



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Abstract

Amino groups are selectively protected in good yields by reaction with O-alkyl S-(pyridin-2-yl)carbonothiolates at room temperature in air. Even substrates with multiple hydroxyl groups such as glucosamine are selectively N-protected.

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Key Words

O-alkyl S-(pyridin-2-yl)carbonothiolates, protective groups, Fmoc protection, Boc protection, Cbz protection, carbamates, N-selective


ID: J72-Y2020