Title:
METHOD FOR OBTAINING HIGH-SELECTIVITY B-CHIRAL BRANCHED-CHAIN CHIRAL AMINO ACID
Document Type and Number:
WIPO Patent Application WO/2023/097691
Kind Code:
A1
Abstract:
Provided is a method for obtaining a high-selectivity β-chiral branched-chain chiral amino acid. The synthetic route of the method for obtaining a high-selectivity β-chiral branched-chain chiral amino acid is: R1 is an alkyl or an aryl; R2 is an alkyl or an aryl; R3 is an alkyl; and R4 is a benzoyl or an acetyl. By using the method for preparing a β-chiral branched-chain chiral amino acid compound, a β-chiral branched-chain chiral amino acid having multiple chiral centers can be efficiently constructed in one step. Different from a traditional enzymatically catalyzed fermentation process, the present solution has better substrate generality and a lower cost, is more environmentally friendly, and can prepare various β-chiral branched-chain chiral amino acid compounds with complex structures.
Inventors:
ZHOU ZHANGTAO (CN)
YE WEIPING (CN)
PHILLIS ANDREW TOROA (CN)
WANG YANG (CN)
WANG DAOGONG (CN)
LUO FUYUAN (CN)
YE WEIPING (CN)
PHILLIS ANDREW TOROA (CN)
WANG YANG (CN)
WANG DAOGONG (CN)
LUO FUYUAN (CN)
Application Number:
PCT/CN2021/135522
Publication Date:
June 08, 2023
Filing Date:
December 03, 2021
Export Citation:
Assignee:
GUANGDONG RAFFLES PHARMATECH CO LTD (CN)
International Classes:
C07C229/36; C07C227/16
Foreign References:
| CN114105793A | 2022-03-01 | |||
| CN1950354A | 2007-04-18 |
Other References:
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BLASER, HANS-ULRICH ET AL.: "(R)-1-[(1R)-1-(Dicyclohexylphosphino) ethyl]-2-(diphenylphosphino)-ferrocene and (2S)-1-[(1R)-1-(Dicyclohexylphosphino) ethyl]-2-(diphenylphosphino)- ferrocene (Josiphos)", ENCYCLOPEDIA OF REAGENTS FOR ORGANIC SYNTHESIS, 14 March 2008 (2008-03-14), XP009546942
YOSHIKAWA NAOKI, TAN LUSHI, MCWILLIAMS J. CHRISTOPHER, RAMASAMY DEEPA, SHEPPARD RUTH: "Catalytic Enantioselective Hydrogenation of N -Alkoxycarbonyl Hydrazones: A Practical Synthesis of Chiral Hydrazines", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 2, 15 January 2010 (2010-01-15), US , pages 276 - 279, XP093071456, ISSN: 1523-7060, DOI: 10.1021/ol902602c
MOLINARO CARMELA, SCOTT JEREMY P., SHEVLIN MICHAEL, WISE CHRISTOPHER, MÉNARD ALAIN, GIBB ANDREW, JUNKER ELLYN M., LIEBERMAN DAVID: "Catalytic, Asymmetric, and Stereodivergent Synthesis of Non-Symmetric β,β-Diaryl-α-Amino Acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 137, no. 2, 21 January 2015 (2015-01-21), pages 999 - 1006, XP093071455, ISSN: 0002-7863, DOI: 10.1021/ja511872a
BUERGLER, JONAS F. ET AL.: "P-Stereogenic Trifluoromethyl Derivatives of Josiphos: Synthesis, Coordination Properties, and Applications in Asymmetric Catalysis", CHEMISTRY - A EUROPEAN JOURNAL, vol. 18, 8 December 2011 (2011-12-08), XP071834580, DOI: 10.1002/chem.201102390
TOGNI, ANTONIO ET AL.: "A Novel Easily Accessible Chiral Ferrocenyldiphosphine for Highly Enantioselective Hydrogenation, Allylic Alkylation, and Hydroboration Reactions", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 116, no. 9, 31 December 1994 (1994-12-31), XP001056531, DOI: 10.1021/ja00088a047
BLASER, HANS-ULRICH ET AL.: "(R)-1-[(1R)-1-(Dicyclohexylphosphino) ethyl]-2-(diphenylphosphino)-ferrocene and (2S)-1-[(1R)-1-(Dicyclohexylphosphino) ethyl]-2-(diphenylphosphino)- ferrocene (Josiphos)", ENCYCLOPEDIA OF REAGENTS FOR ORGANIC SYNTHESIS, 14 March 2008 (2008-03-14), XP009546942
YOSHIKAWA NAOKI, TAN LUSHI, MCWILLIAMS J. CHRISTOPHER, RAMASAMY DEEPA, SHEPPARD RUTH: "Catalytic Enantioselective Hydrogenation of N -Alkoxycarbonyl Hydrazones: A Practical Synthesis of Chiral Hydrazines", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 2, 15 January 2010 (2010-01-15), US , pages 276 - 279, XP093071456, ISSN: 1523-7060, DOI: 10.1021/ol902602c
Attorney, Agent or Firm:
BEIJING ORIGINTELLIGENCE IP LAW FIRM (CN)
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