Title:
SYNTHESIS METHOD FOR α-AZIDO KETONE CONTAINING TERTIARY STEREOCENTER
Document Type and Number:
WIPO Patent Application WO/2024/017221
Kind Code:
A1
Abstract:
A synthesis method for an α-azido ketone containing a tertiary chiral center, the synthesis method comprising: under the action of a squaramide catalyst, reacting a sulfoxonium ylide derivative with an azidation reagent HN3 generated in situ from TMSN3 and a proton source, so as to generate the α-azido ketone. The reaction conditions are mild, and no metal is needed; and the method has good yield and enantiomeric selectivity.
Inventors:
GUO WENGANG (CN)
ZHOU YING (CN)
LE XIN (CN)
JIANG FENG (CN)
ZHOU YING (CN)
LE XIN (CN)
JIANG FENG (CN)
Application Number:
PCT/CN2023/107817
Publication Date:
January 25, 2024
Filing Date:
July 18, 2023
Export Citation:
Assignee:
UNIV CHANGZHOU (CN)
International Classes:
C07D333/22; C07C247/10; C07D307/52
Foreign References:
| CN115108937A | 2022-09-27 | |||
| US3821277A | 1974-06-28 |
Other References:
GUO WENGANG, JIANG FENG, LI SHIJIA, SUN JIANWEI: "Organocatalytic asymmetric azidation of sulfoxonium ylides: mild synthesis of enantioenriched α-azido ketones bearing a labile tertiary stereocenter", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 13, no. 39, 12 October 2022 (2022-10-12), United Kingdom , pages 11648 - 11655, XP093130640, ISSN: 2041-6520, DOI: 10.1039/D2SC03552A
PATONAY TAMOS, HOFFMAN ROBERT V.: "A General and Efficient Synthesis of .alpha.-Azido Ketones", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 59, no. 10, 1 May 1994 (1994-05-01), pages 2902 - 2905, XP093130642, ISSN: 0022-3263, DOI: 10.1021/jo00089a043
DAY DAVID PHILIP, MORA VARGAS JORGE ANDRÉS, BURTOLOSO ANTONIO CARLOS BENDER: "Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 17, 3 September 2021 (2021-09-03), pages 12427 - 12435, XP093130645, ISSN: 0022-3263, DOI: 10.1021/acs.joc.1c01441
PATONAY TAMOS, HOFFMAN ROBERT V.: "A General and Efficient Synthesis of .alpha.-Azido Ketones", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 59, no. 10, 1 May 1994 (1994-05-01), pages 2902 - 2905, XP093130642, ISSN: 0022-3263, DOI: 10.1021/jo00089a043
DAY DAVID PHILIP, MORA VARGAS JORGE ANDRÉS, BURTOLOSO ANTONIO CARLOS BENDER: "Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 17, 3 September 2021 (2021-09-03), pages 12427 - 12435, XP093130645, ISSN: 0022-3263, DOI: 10.1021/acs.joc.1c01441
Attorney, Agent or Firm:
CHANGZHOU INNOVATION PATENT AGENCY (CN)
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