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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 5-6
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Original Articles

Novel Chiral Building Block: (2R,3S)-2-(1,3-Dithian-2-yl)-3-hydroxybutanoates. Highly Diastereo- and Enantioselective Baker's Yeast Reduction of 2-(1,3-Dithian-2-yl)-3-oxobutanoates

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Pages 1119-1124 | Received 23 Jun 1988, Published online: 24 Oct 2006

References

  • Sih , C. J. and Chen , C. S. 1984 . Angew. Chem., Int. Ed. Engl. , 23 : 570
  • Buisson , D. and Azerad , R. 1986 . Tetrahedron Lett. , 27 : 2631 D. Buisson, C. Sanner, M. Larcheveque, and R. Azerad, ibid., 28, 3939 (1987); and references cited therein.
  • Stahl , I. 1985 . Chem. Ber. , 118 : 3159
  • House , H. O. , Crumrine , D. S. , Teranishi , A. Y. and Olmstead , H. D. 1973 . J. Am. Chem. Soc. , 95 : 3310 The coupling constant (Jαβ) of anti isomer (J=10.0 Hz) is greater than that of syn isomer (J=7.6 Hz). Cf..
  • Dale , J. A. 1969 . J. Org. Chem. , 34 : 2543 The (3S)-isomers always show upfield signals (doublet) for the terminal-CH3 resonances (e.g., 2a: 1.43 vs. 1.34 ppm, 2b: 1.44 vs. 1.37 ppm). Cf..
  • The relative stereochemistry was determined after conversion into the corresponding methyl ester; see ref. 4.
  • Absolute configuration at the hydroxylated carbon and enantiomeric excess were determined by 1H NMR study of the corresponding (+)-MTPA ester; See ref. 5.

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