Improved Stereoselectivity in Intramolecular SN2′ Cyclization through Use of Mechanistic Principles

Woo Duck Seo; Marcus J. Curtis-Long; Seong Hun Jeong; Tae Hong Jun; Min Suk Yang; Ki Hun Park

doi:10.1055/s-2006-958956

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Synthesis 2007(2): 209-214
DOI: 10.1055/s-2006-958956

PAPER

Improved Stereoselectivity in Intramolecular S_N2′ Cyclization through Use of Mechanistic Principles

Woo Duck Seo^a, Marcus J. Curtis-Long^b, Seong Hun Jeong^a, Tae Hong Jun^a, Min Suk Yang^a, Ki Hun Park*^a
^a Division of Applied Life Science (BK 21 Program), Institute of Agriculture & Life Sciences, Department of Agricultural Chemistry, Gyeongsang National University, Jinju 660-701, South Korea
Fax: +82(55)7570178; e-Mail: khpark@gshp.gsnu.ac.kr;
^b Woodview, 12 New Road, Nafferton, East Yorkshire, YO25 4JP, UK

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Publication History

Received 28 August 2006
Publication Date:
21 December 2006 (online)

Abstract
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Abstract

Valine and alanine were converted into the corresponding α-hydroxy-β-amino acids through intramolecular S_N2′ cyclization. The novel cyclization protocol relied upon the use of N-benzyl-protected carbamates derived from α-amino acids

Key words

oxazolidin-2-one - intramolecular cyclization - stereoselectivity - A(1,3) strain - α-hydroxy-β-amino acids

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