Logo image
Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group
Journal article   Peer reviewed

Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group

Barry M. Trost, Christopher A. Kalnmals, Jacob S. Tracy and Wen-Ju Bai
Organic letters, Vol.20(24), pp.8043-8046
12/21/2018
PMID: 30511873
Web of Science ID: WOS:000454567800067

Metrics

Abstract

Nonreducing, pH -neutral conditions for the selective cleavage of the 2,2,2-trichloroethoxycarbonyl (Troc) protecting group are reported. Using trimethyltin hydroxide in 1,2-dichloroethane, Troc-protected alcohols, thiols, and amines can be selectively unmasked in the presence of various functionalities that are incompatible with the reducing conditions traditionally used to remove the Troc group. This mild deprotection protocol tolerates a variety of other hydrolytically sensitive and acid/base-sensitive moieties as well.

Details

Logo image