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

Woo Duck Seo; Marcus J. Curtis-Long; Jin Hyo Kim; Jong Keun Park; Ki Min Park; Ki Hun Park

doi:10.1055/s-2005-872264

LETTER

Highly Stereoselective Intramolecular S_N2′ Cyclization Yielding Chiral Oxazolidin-2-ones: General Route to α-Hydroxy-β-amino Acids

Woo Duck Seo^a, Marcus J. Curtis-Long^b, Jin Hyo Kim^a, Jong Keun Park^c, Ki Min Park^d, 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;

Abstract

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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 S_N2′ cyclization - AHPBA - silica gel - α-hydroxy-β-amino acids

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References

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

Highly Stereoselective Intramolecular S_N2′ Cyclization Yielding Chiral Oxazolidin-2-ones: General Route to α-Hydroxy-β-amino Acids