Asymmetric synthesis of aryloxypropanolamines via OsO 4-catalyzed asymmetric dihydroxylation

A simple and effective procedure for the enantioselective synthesis of several β-adrenergic blocking agents incorporating the first asymmetric synthesis of celiprolol, is described. The key steps are (i) sharpless asymmetric dihydroxylation of aryl allyl ethers to introduce chirality into the molecu...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 61; no. 11; pp. 2831 - 2838
Main Authors Sayyed, Iliyas A., Thakur, Vinay V., Nikalje, Milind D., Dewkar, Gajanan K., Kotkar, S.P., Sudalai, A.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2005
Subjects
Antihypertensive
Asymmetric dihydroxylation
Cyclic sulfates
Epoxides
Antihypertensive
Asymmetric dihydroxylation
Cyclic sulfates
Epoxides
Online AccessGet full text

Cover

More Information
Summary:A simple and effective procedure for the enantioselective synthesis of several β-adrenergic blocking agents incorporating the first asymmetric synthesis of celiprolol, is described. The key steps are (i) sharpless asymmetric dihydroxylation of aryl allyl ethers to introduce chirality into the molecules and (ii) conversion of cyclic sulfates into the corresponding epoxides using a three-step procedure. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.01.074