M. Sakaitani, Y. Ohfune
Feb 1, 1990
Citations
1
Influential Citations
187
Citations
Quality indicators
Journal
Journal of Organic Chemistry
Abstract
The N-tert-butyldimethylsilyloxycarbonyl group (silyl carbamate) was synthesized from commonly used amino protecting groups such as N-tert-butoxycarbonyl (Boc) and N-benzyloxycarbonyl (Z) by treatment with tert-butyldimethylsilyl trifluoromethanesulfonate/2,6-lutidine and tert-butyldimethylsilane/Pd(OAc) 2 , respectively. This novel species, upon activation with fluoride ion, reacts with a variety of electrophiles to give N-ester type compounds in high yield. For example, the conversion of N-t-Boc compounds into their corresponding N-Z compounds via a silyl carbamate was accomplished under these mild reaction conditions