Highly Diastereoselective Reduction of New Chiral α-Ketoamides

References

• Munegumi , T. and Harada , K. 1983 . Chem. Lett. , : 1225
   Web of Science ®Google Scholar
• Soai , K. and Hasegawa , H. 1985 . J. Chem. Soc., Perkin Trans. I , : 769
   Google Scholar
• Kawanami , Y. , Fujita , I. , Taniguchi , Y. , Katsuki , T. and Yamaguchi , M. 1987 . Chem. Lett. , : 2021
   Web of Science ®Google Scholar
• Kawanami , Y. , Fujita , I. , Asahara , S. , Katsuki , T. and Yamaguchi , M. 1989 . Bull. Chem. Soc. Jpn. , 62 : 3598
   Web of Science ®Google Scholar
• Solodin , I. , Goldberg , Y. , Zelcans , G. and Lukevics , E. 1990 . J. Chem. Soc., Chem. Commun. , : 1321
   Google Scholar
• Solladie-Cavallo , A. and Suffert , J. 1985 . Tetrahedron Lett. , 26 : 429
   Web of Science ®Google Scholar
• Boireau , G. and Deberly , A. 1991 . Tetrahedron Asymmetry , 2 : 771
   Google Scholar
• Akiyama , T. , Nishimoto , H. and Ozaki , S. 1991 . Tetrahedron Lett. , 32 : 1335
   Web of Science ®Google Scholar
• Xiang , Y. B. , Snow , K. and Belley , M. 1993 . J. Org. Chem. , 58 : 993
   Web of Science ®Google Scholar
• Corey , E. J. , McCaully , R. J. and Sachdev , H. S. 1970 . J. Am. Chem. Soc. , 92 : 2476
   PubMed Web of Science ®Google Scholar
• Corey , E. J. , Sachdev , H. S. , Gougoutas , J. Z. and Saenger , W. 1970 . J. Am. Chem. Soc. , 92 : 2488
   PubMed Web of Science ®Google Scholar
• Kim , Y. H. , Park , D. H. , Byun , I. S. , Yoon , I. K. and Park , C. S. 1993 . J. Org. Chem. , 58 : 4511
   Web of Science ®Google Scholar
• Kim , Y. H. , Kim , S. H. and Park , D. H. 1993 . Tetrahedron Lett. , 34 : 6063
   Web of Science ®Google Scholar
• The % ee was determined by 1H NMR and HPLC analysis using (R)-(+)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (Mosher's reagent).
   Google Scholar
• Fujisawa , T. , Ukaji , Y. , Funaboro , M. , Yamashita , M. and Sato , T. 1990 . Bull. Chem. Soc. Jpn. , 63 : 1894
   Web of Science ®Google Scholar
• Hydrolysis for 2a was carried out using similar experimental procedure (73%) : [α]D 22=- 13.3° (c 1.53, 1.5 M NaOH), [literature, [α]D=- 13.5° (c 2.5, 1.5 M NaOH). Benzoylformamide 2b obtained in 98% de was hydrolyzed to give (S)-mandelic acid of 93.7% ee; [α]D 22=+ 148° (c 1.10, H2O), [literature, [α]D=+ 158 (H2O)]. Unlike aliphatic α-hydroxyamide, aromatic α-hydroxyamide has been known to epimerize partially during the acidic hydrolysis because of the electron withdrawing effect of the phenyl group.1c,1d
   Google Scholar