Scope and Limitations of an Acid Catalyzed Protocol for Hypersilyl Protection of Alcohols

A highly efficient and convenient triflic acid (TfOH) catalyzed protocol for the protection of various functionalized alcohols in CH2Cl2 at ambient temperature using tris(trimethylsilyl)silyl-N,N-dimethyl-methaneamide (hypersilylamide) 1 as the protecting reagent is developed. Herein, results on the scope and limitations of this protocol for a number of functionalized alcohols are presented. This method was found to be effective for the selective protection of less hindered OH groups in different classes of diols containing both pri/tert, sec/tert, or aromatic/aliphatic hydroxyl groups. In general, our protocol exhibited excellent functional group tolerance in the protection of alcohols containing alkoxy, keto, amino, as well as halo substituents in good to excellent yields.

Anas, SaithalaviUppsala universitet,Institutionen för kemi - BMC (author)
Emanuelsson, RikardUppsala universitet,Institutionen för kemi - BMC (author)
Lozinski, KaitlinDisciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC) and Department of Chemistry, University of Richmond, UR 1099, 28 Westhampton Way, VA 23173, USA,Department of Chemistry-BMC (author)
Ottosson, HenrikUppsala universitet,Institutionen för kemi - BMC (author)
Uppsala universitetInstitutionen för kemi - BMC (creator_code:org_t)

By the author/editor: Alvi, Muhammad R ...; Anas, Saithalavi; Emanuelsson, Rik ...; Lozinski, Kaitli ...; Ottosson, Henrik

About the subject

NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

Kungliga biblioteket hanterar dina personuppgifter i enlighet med EU:s dataskyddsförordning (2018), GDPR. Läs mer om hur det funkar här.
Så här hanterar KB dina uppgifter vid användning av denna tjänst.