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Synthesis 2012(4): 561-568  
DOI: 10.1055/s-0031-1289677
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Five-, Six-, and Seven-Membered Heterocycles from (S)-3-Hydroxy-γ-butyrolactone

Hao Yang, Navneet Goyal, Jean Rene Ella-Menye, Kristopher Williams, Guijun Wang*
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Fax: +1(504)2806860; e-Mail: gwang2@uno.edu ;
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Publikationsverlauf

Received 26 October 2011
Publikationsdatum:
30. Januar 2012 (online)

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Abstract

Chiral small molecules such as amino alcohols and their heterocyclic derivatives are useful building blocks for asymmetric synthesis and the preparation of biologically active compounds. Using a common starting material derived from carbohydrate, the (S)-3-hydroxy-γ-butyrolactone, we have synthesized several five-, six-, and seven-membered nitrogen-containing chiral heterocycles. These include (S)-3-benzyloxypyrrolidine, a protected 6-substituted morpholin-3-one and its homologous 1,4-oxazepan-3-one, and 6-trityloxymethyl tetrahydro-1,3-oxazine-2-thiones. These chiral small heterocycles were synthesized from the lactone via efficient cyclization reactions. Their syntheses and characterization are reported here.

Key words

amino alcohols - heterocycles - cyclization - lactones - chiral pool - asymmetric synthesis

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