Trimethylsilyl trifluoromethanesulfonate (TMSOTf) assisted facile deprotection of N,O-acetonides.
Employing TMSOTf as an easily available reagent, we have developed a mild and efficient method for the deprotection of both terminal and internal N,0-acetonide functionalities. Various regularly used protecting groups and common organic functional moieties were found to be unaffected by the described reaction conditions. In a few representative examples, the present method was also extended to deprotect acetonides obtained from 1,2-, and 1,3-terminal diols. The acetonide deprotection protocol described herein is expected to be a useful addition to the presently available methods for performing the above transformation.
Poon
Kevin W C
KW
Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Lovell
Kimberly M
KM
Dresner
Kendra N
KN
Datta
Apurba
A
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000438:Alcohols; D006571:Heterocyclic Compounds; D008698:Mesylates; D013141:Spiro Compounds; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate