Method for the production of chiral vicinal aminoalcohols

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing nitrogen-containing organic compound

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

435280, C12P 1300, C12P 4100

Patent

active

058342613

ABSTRACT:
The disclosure describes a method for the preparation of chiral vicinal aminoalcohols in high optical purity. The method combines the stereoselective reduction of the keto group of a .beta.-ketoacid, .beta.-keotester, or derivative with the stereospecific rearrangement of the corresponding amide, hyroxamic acid, or hydrazide to produce chiral vicinal aminoalcohols with control of stereochemistry at both chiral centers.

REFERENCES:
Didier et al., "Chemo-enzymatic synthesis of 1,2-and 1,3-amino alcohols and their use in the enantioselective reduction of acetophenone and anti-acetophenone oxime methyl ether with borane", Tetrahedron 47 (27): 4941-58 (1991).
Gotor, "Enzymic aminolysis, hydrazinolysis and oximolysis reactions", NATO ASI Ser., Ser. C 381 : 199-208 (1992).
Pedrocchi-Fantoni et al., "Chiral amino alcohols from baker's yeast reduction of alpha keto acid derivatives", Gazz. Chim. Ital. 122 (12): 499-502 (1992).
Geissman, T.A., Rearrangements Involving Electron-deficient Nitrogen in Principles of Organic Chemistry (W. H. Freeman & Co., 1962), pp. 674-675.
1992, C. Bull et al in "Biocatalytic Production of Amino Acids and Derivatives", D. Ruzzolard F. Wagner, Eds., pp. 255-256.
1992, "Preparative Biotransformations," S.M. Roberts, Ed. Chapter 2.
1996, A.K. Saksena et al, "Tetrahedron letters", 37 5657-5660.
1948, Tullar, B. F., J. Am. Chem. Soc. 70, 2067-2068.
1986, D. Buisson and R. Azerad, Tetrahedron Letters, 27, 2631-2634.
1990, S. Servi, Synthesis pp. 1-25.
1985, D. Seebach et al, Organic Synthesis, 63, pp. 1-9.
1987, D. W. Brooks and K. W. Woods, J. Org. Chem., 52, 2036-2039.
1988, A. Fauve and H. Veschambre, J. Org. Chem., 53, 5215-5219.
1978, M. Bucciarelli et al, J. Chem. Soc. Chem. Comm., pp. 456-457.
1984, K. Kieslich in Biotransformations, vol. 6a, Chapter O.
1980, Z. Shaked and G.M. Whitesides, J. Am. Chem. Soc. 102, 7104-7105.
1984, J. B. Jones and T. Takemura, Canadian J. Chem., 62, 77-80.
1949, E. S. Willis and J. F. Lane, Organic Reactions III., Chapter 7, pp. 267-306.
1969, P.A.S. Smith, Trans. N.Y. Acad. Sci, 31, 504-515.
1973, S. Simons, Jr., J. Org. Chem, 38, 414-416.
1976, W.L.F. Armarego et al, J. Chem. Soc. Perkin Trans., I, 2229-2237.
1974, S. Bittner et al., Tetrahedron Letters, 23, 1965-1968.
1974, L. Bauer and O. Exner, Angew. Chem. Int. Edition, 13 376-384.
1946, P.A.S. Smith, Organic Reactions. III, Chapter 9, pp. 337-338.
1948, J. M. Saunders and R. J. Slocombe, Chem. Rev. 43, 203-218.
1971, D. V. Banthorpe in "The Chemistry of the Azido Group", Chapter 7, pp. 397-405.
1980, J. D. Warren and J. B. Press, Synth. Communications, 10, 107-110.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Method for the production of chiral vicinal aminoalcohols does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for the production of chiral vicinal aminoalcohols, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for the production of chiral vicinal aminoalcohols will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1515590

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.