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Synlett 2005(15): 2289-2292  
DOI: 10.1055/s-2005-872264
LETTER
© Georg Thieme Verlag Stuttgart · New York

Highly Stereoselective Intramolecular SN2′ Cyclization Yielding Chiral ­Oxazolidin-2-ones: General Route to α-Hydroxy-β-amino Acids

Woo Duck Seoa, Marcus J. Curtis-Longb, Jin Hyo Kima, Jong Keun Parkc, Ki Min Parkd, 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
b Trout Beck, Wansford, Driffield, East Yorkshire, YO25 8NX, UK
c Department of Chemical Education, Gyeongsang National University, Jinju 660-701, South Korea
d The research Institute of Natural Science, Gyeongsang National University, Jinju 660-701, South Korea
Fax: +82(55)7570178; e-Mail: khpark@gshp.gsnu.ac.kr;
Further Information

Publication History

Received 21 June 2005
Publication Date:
03 August 2005 (online)

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Abstract

Intramolecular nucleophilic attack onto allylsulfonates promoted by silica gel acting as an acid catalyst provides expedient stereoselective access to 4,5-difunctionalized oxazolidin-2-ones. Precursors were prepared efficiently from enantiopure α-amino ­acids and subsequent manipulation of the oxazolidin-2-ones yielded enantiopure α-hydroxy-β-amino acids.

Key words

oxazolidin-2-one - intramolecular SN2′ cyclization - AHPBA - silica gel - α-hydroxy-β-amino acids

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The structure was solved by direct methods and refined by full matrix least-squares against F ² for all data using the SHELXTL program package. CCDC reference number 275654. The crystal structure has been deposited at the Cambridge Crystallographic Data Centre.