WO2000015605A3 - Chiral cyanoamines and methods of preparation - Google Patents

Chiral cyanoamines and methods of preparation Download PDF

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Publication number
WO2000015605A3
WO2000015605A3 PCT/US1999/021020 US9921020W WO0015605A3 WO 2000015605 A3 WO2000015605 A3 WO 2000015605A3 US 9921020 W US9921020 W US 9921020W WO 0015605 A3 WO0015605 A3 WO 0015605A3
Authority
WO
WIPO (PCT)
Prior art keywords
cyanoamines
optically enriched
preparation
methods
chiral
Prior art date
Application number
PCT/US1999/021020
Other languages
French (fr)
Other versions
WO2000015605A2 (en
Inventor
Amir H Hoveyda
Marc L Snapper
Kevin Kuntz
Clinton A Krueger
Carolyn Dzierba
Original Assignee
Trustees Boston College
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Trustees Boston College filed Critical Trustees Boston College
Publication of WO2000015605A2 publication Critical patent/WO2000015605A2/en
Publication of WO2000015605A3 publication Critical patent/WO2000015605A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • C07K1/047—Simultaneous synthesis of different peptide species; Peptide libraries
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

The present invention relates to chiral catalysts that can be used to transform chemically compatible imines to optically enriched cyanoamines, to the application of such catalysts to the synthesis of optically enriched cyanoamines, and to the preparation of optically enriched amino acids, optically enriched amino alcohols, or optically enriched diamines. In general, catalysts useful in the methods of the invention have the structure (Formula I), where the different groups Ar, U, V, W, X, Y, Z, R1, R2, R3, M, L and n have the meanings defines in the description.
PCT/US1999/021020 1998-09-14 1999-09-14 Chiral cyanoamines and methods of preparation WO2000015605A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10029498P 1998-09-14 1998-09-14
US60/100,294 1998-09-14

Publications (2)

Publication Number Publication Date
WO2000015605A2 WO2000015605A2 (en) 2000-03-23
WO2000015605A3 true WO2000015605A3 (en) 2000-05-25

Family

ID=22279058

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/021020 WO2000015605A2 (en) 1998-09-14 1999-09-14 Chiral cyanoamines and methods of preparation

Country Status (1)

Country Link
WO (1) WO2000015605A2 (en)

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
B M COLE ET AL.: "Discovery of chiral catalysts through ligand diversity; Ti-catalyzed enantioselective addition of TMSCN to meso epoxides", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 35, no. 15, 19 August 1909 (1909-08-19), VERLAG CHEMIE. WEINHEIM., DE, pages 1668 - 1671, XP002131539, ISSN: 0570-0833 *
C A KRUEGER ET AL.: "Ti-catalyzed enantioselective addition of cyanide to imines. A practical synthesis of optically pure alpha-amino acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 121, no. 17, 5 May 1999 (1999-05-05), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 4284 - 4285, XP002131541, ISSN: 0002-7863 *
CHEMICAL ABSTRACTS, vol. 91, no. 3, 16 July 1979, Columbus, Ohio, US; abstract no. 21044, K JARASIMHULU & R A DAY: "Nitrile elimination and hydrogen rearrangement upon electron impact upon Schiff base peptide esters" XP002131542 *
K D SHIMIZU ET AL.: "Search for chiral catalysts through ligand diversity; substrate-specific catalysts and ligand screening on solid phase", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 36, no. 16, 18 August 1997 (1997-08-18), VERLAG CHEMIE. WEINHEIM., DE, pages 1704 - 1707, XP002131538, ISSN: 0570-0833 *
M S SIGMAN & E N JACOBSEN: "Schiff base for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 120, no. 19, 20 May 1998 (1998-05-20), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 4901 - 4902, XP000857794, ISSN: 0002-7863 *
ORG. MASS SPECTROM., vol. 13, no. 9, 1983, pages 540 - 543 *

Also Published As

Publication number Publication date
WO2000015605A2 (en) 2000-03-23

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