Publication:
Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction

1

Issued Date

2007-09-03

Resource Type

Article

ISSN

00404020

DOI

10.1016/j.tet.2007.06.047

Other identifier(s)

2-s2.0-34447622684

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron. Vol.63, No.36 (2007), 8727-8734

Suggested Citation

Vorawit Banphavichit, Worawan Bhanthumnavin, Tirayut Vilaivan Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction. Tetrahedron. Vol.63, No.36 (2007), 8727-8734. doi:10.1016/j.tet.2007.06.047 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/24123

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Title

Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction

Author(s)

Vorawit Banphavichit
 Worawan Bhanthumnavin
 Tirayut Vilaivan

Other Contributor(s)

Mahidol University

Abstract

A one-step, multicomponent Mannich-type reaction between phenols, paraformaldehyde, and β-aminoalcohols in the presence of LiCl afforded N-2-hydroxybenzyloxazolidines with high ortho-selectivity. Hydrolytic or reductive ring opening of the oxazolidines provided a series of N-salicyl-β-aminoalcohols in 84-92% overall yield. The synthesized compounds were evaluated as ligands for a titanium-catalyzed catalytic asymmetric Strecker reaction. The reaction employing 10 mol % of catalyst provided the Strecker products in excellent yields and up to 98% ee. © 2007 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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URI

https://repository.li.mahidol.ac.th/handle/123456789/24123

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Scopus 2006-2010