Enantioselective Silicon-Mediated Synthesis of Glyceraldehyde Derivatives from Propargyl Alcohol

References

• McGarvey , G. J. , Kimura , M. , Oh , T. and Williams , J. M. 1984 . J. Carbohydrate Chem. , 3 : 125 For reviews, see:
   Web of Science ®Google Scholar
• Jurczak , J. , Pikul , S. and Bauer , T. 1986 . Tetrahedron , 42 : 447
   Web of Science ®Google Scholar
• Baer , E. and Fischer , H. O. L. 1939 . J. Biol. Chem. , 128 : 463
   Google Scholar
• Hertel , L. W. , Grossman , C. S. and Kronin , J. S. 1991 . Synth. Comm. , 21 : 151 For a recent studies on this synthesis, see:
   Web of Science ®Google Scholar
• Schmid , C. R. , Bryant , J. D. , Dowlatzedah , M. , Philips , J. L. , Prather , D. E. , Schantz , R. D. , Sear , N. L. and Vianco , C. S. 1991 . J. Org. Chem. , 56 : 4056
   Web of Science ®Google Scholar
• Katsuki , T. and Sharpless , K. B. 1980 . J. Am. Chem. Soc. , 102 : 5974
   Web of Science ®Google Scholar
• Hanson , R. M. 1991 . Chem. Rev. , 91 : 437 For a review on glycidols, see:
   Web of Science ®Google Scholar
• Ko , S. Y. , Lee , A. W. M. , Masamune , S. , Reed , L. A. III , Sharpless , K. B. and Walker , F. J. 1990 . Tetrahedron , 46 : 245 and references cited therein
   Web of Science ®Google Scholar
• Kang , S-k. and Shin , D-O. 1986 . Bull. Korean Chem. Soc. , 7 : 159
   Google Scholar
• Ko , S. Y. , Masamune , H. and Sharpless , K. B. 1987 . J. Org. Chem. , 52 : 667
   Web of Science ®Google Scholar
• Gao , Y. , Hanson , R. M. , Klunder , J. M. , Ko , S. Y. , Masamune , H. and Sharpless , K. B. 1987 . J. Am. Chem. Soc. , 109 : 5765
   Web of Science ®Google Scholar
• Jones , T. K. and Denmark , S. E. 1986 . Org. Synth. , 64 : 182
   Google Scholar
• Katsuki , T. 1984 . Tetrahedron Lett. , 25 : 2821
   Web of Science ®Google Scholar
• In the Katsuki paper (ref. 10) the configuration of epoxide obtained from 4 with the use of (-)-diisopropyl tartrate is assigned erroneously as (2S,3S) [should be (2R,3R)]
   Google Scholar
• Signals of the other enantiomer were not detectable in the spectra (comparison was made to the product derived from racemic material)
   Google Scholar
• Upon the use of MeOH as solvent in the hydrolysis, according to the original procedure,8 the product was contaminated with methyl pnitrobenzoate which was difficult to remove.
   Google Scholar
• Dale , J. A. , Dull , D. L. and Mosher , H. S. 1969 . J. Org. Chem. , 34 : 2543
   Web of Science ®Google Scholar
• Bassindale , A. R. and Taylor , P. G. 1989 . “The Chemistry of Organic Silicon Compounds” , Edited by: Patai , S. and Rappoport , Z. 951 Chichester : Wiley .
   Google Scholar
• Colvin , E. W. 1981 . “Silicon in Organic Synthesis” , London : Butterworth .
   Google Scholar
• Jankowski , P. , Marczak , S. , Masnyk , M. and Wicha , J. 1991 . J. C. S. Chem. Commun. , : 297
   Google Scholar
• Achmatowicz , B. , Wicha , J. , Hudrlik , P. F. , Hudrlik , A. and Kulkarni , A. K. 1985 . Tetrahedron Lett. , 26 : 139 unpublished results; for some examples of the vinylamines and enolethers synthesis from α,ß-epoxyalkylsilanes, see: a.
   Google Scholar
• Fleming , I. and Newton , T. W. 1984 . J. Chem. Soc. Perkin , 1 : 119
   Google Scholar
• Stork , G. and Colvin , E. 1971 . J. Am. Chem. Soc. , 93 : 2080
   Google Scholar
• Boeckmann , R. K. and Bruza , K. J. 1974 . Tetrahedron Lett. , : 3365
   Google Scholar
• An account on silica gel-catalyzed addition benzenethiol to others α,ß-epoxysilanes and to epoxides will be published elsewhere
   Google Scholar
• Ager , D. J. and Cookson , R. C. 1980 . Tetrahedron Lett. , 21 : 1677
   Google Scholar
• Ager , D. J. 1983 . J. Chem. Soc. Perkin , 1 : 1135
   Google Scholar
• Parham , W. E. and Edwards , L. D. 1968 . J. Org. Chem. , 33 : 4150
   Google Scholar
• Iriuchijima , S. , Maniwa , K. and Tsuchihashi , G. 1974 . J. Am. Chem. Soc. , 96 : 4280
   Web of Science ®Google Scholar
• Oi , R. and Sharpless , K. B. 1992 . Tetrahedron Lett. , 33 : 2095 After described hirein work has been completed, another method of the glyceraldehyde derivatives synthesis was published:
   Google Scholar
• Pure 2,3-isopropylidene-D-glyceraldehyde (1) shows [α]D +80.1° (c 1.53 benzene); for comments on distillation and stability of monomeric compound 1, see ref. 3b.
   Google Scholar