One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols

Author:

Bergueiro Julián1234,Montenegro Javier534,Saá Carlos534,López Susana1234

Affiliation:

1. Departamento de Química Orgánica

2. Facultade de Química

3. Universidad de Santiago de Compostela

4. Santiago de Compostela, Spain

5. Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS)

Abstract

A novel chemoselective one-pot transformation of acetals to silyl ethers is reported. Free hydroxyls, double bonds and triple bonds are unaffected in optimal reaction conditions. This practical, inexpensive protocol allows the selective replacement of acetal-forming protecting groups with silyl groups in a single step under mild conditions.

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Reference34 articles.

1. T. V. Greene and P. G. M.Wuts , Protective Groups in Organic Synthesis , John Wiley and Sons , New York , 3rd edn, 1991 , p. 17 and 297

2. I. Fleming , Protecting groups , Grog Thieme , New York , 1994 , p. 21

3. J. R. Hanson , Protective Groups in Organic Synthesis , Blackwell Science Inc. , Malden, MA , 1st edn, 1999 , p. 37

4. Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis

5. Symmetrical alkoxysilyl ethers. A new class of alcohol-protecting groups. Preparation of tert-butoxydiphenylsilyl ethers

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