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

Alvi, Muhammad RoufUppsala universitet,Institutionen för kemi - BMC (författare)

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 (författare)
Emanuelsson, RikardUppsala universitet,Institutionen för kemi - BMC (författare)
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 (författare)
Ottosson, HenrikUppsala universitet,Institutionen för kemi - BMC (författare)
Uppsala universitetInstitutionen för kemi - BMC (creator_code:org_t)

Av författaren/redakt...: Alvi, Muhammad R ...; Anas, Saithalavi; Emanuelsson, Rik ...; Lozinski, Kaitli ...; Ottosson, Henrik

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