Diastereoselective reduction of chiral N-tosyl 2-benzoyl-1,3-oxazines derived from D-glucose

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 407-410

  Ko, Kwang Youn ^a   Park, Jong Yek ^a  

^a Ajou University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 OXAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0031032975     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02311-8     Document Type: Article

References (18)

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8. However, see ref. 1 (g) as an exception.
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11. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons, Inc: New York, 1995; pp. 64-67.
12. For the recent review on the use of carbohydrates as chiral auxiliaries, see Kunz, H.; Rück, K. Angew. Chem. Int. Ed. Engl. 1993, 32, 336-358. However, to the best of our knowledge the use of compounds 2 as chiral auxiliaries has not been reported in the literature.
13. Satisfactory spectroscopic and analytical data were obtained for all new compounds.
14. Vogel, A. I. Vogel's Textbook of Practical Organic Chemistry, Longman Scientific and Technical: Harlow, 1989; pp. 663-664.
15. Diol 1b was prepared from (+)-(4,6-O-benzylidene)methyl-α-D-glucopyranoside as shown in the following scheme. Equation presented.
16. Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843-2846.
17. Aldrich Catalog Handbook of Fine Chemicals 1996-1997; Aldrich Chemical Co., Inc.: Milwaukee, 1996.
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