Formate and CO 2 Enable Reductive Carboxylation of Imines: Synthesis of Unnatural α-Amino Acids

Herein, a photocatalytic umpolung strategy for reductive carboxylation of imines for the synthesis of α-amino acids was disclosed. Carbon dioxide radical anion (CO ) generated from formate is the key single electron reductant in the reactions. An unprecedentedly broad substrate scope of imines with...

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Published inJournal of organic chemistry Vol. 89; no. 14; pp. 9750 - 9754
Main Authors Xu, Pei, Liu, Wen-Wen, Hao, Tian-Zi, Liu, Yi-Qin, Jiang, Hui-Xian, Xu, Jing, Li, Jin-You, Yin, Long, Zhu, Song-Lei, Zhu, Xu
Format Journal Article
LanguageEnglish
Published United States 19.07.2024
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Abstract Herein, a photocatalytic umpolung strategy for reductive carboxylation of imines for the synthesis of α-amino acids was disclosed. Carbon dioxide radical anion (CO ) generated from formate is the key single electron reductant in the reactions. An unprecedentedly broad substrate scope of imines with excellent reaction yields was obtained with carbon dioxide (CO ) and formate salt as carbon sources.
AbstractList Herein, a photocatalytic umpolung strategy for reductive carboxylation of imines for the synthesis of α-amino acids was disclosed. Carbon dioxide radical anion (CO ) generated from formate is the key single electron reductant in the reactions. An unprecedentedly broad substrate scope of imines with excellent reaction yields was obtained with carbon dioxide (CO ) and formate salt as carbon sources.
Author Hao, Tian-Zi
Jiang, Hui-Xian
Yin, Long
Xu, Jing
Xu, Pei
Zhu, Xu
Liu, Yi-Qin
Liu, Wen-Wen
Zhu, Song-Lei
Li, Jin-You
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Cites_doi 10.1038/s41467-018-07351-2
10.31635/ccschem.020.202000374
10.1002/asia.201900379
10.1002/anie.201806874
10.1016/j.chempr.2021.08.004
10.1038/s41929-022-00841-z
10.1021/acs.orglett.2c01533
10.1021/acscatal.3c04125
10.1016/S1872-2067(23)64468-7
10.1021/acscatal.2c06377
10.1016/j.scib.2023.11.018
10.1039/D3GC02955G
10.1007/s11426-022-1554-x
10.1021/acs.orglett.2c01267
10.1021/jacs.0c03144
10.1021/j100300a045
10.1021/cr9300348
10.1002/cctc.202300695
10.1021/acs.accounts.9b00621
10.1016/S1872-2067(22)64140-8
10.1002/chem.201604623
10.1021/jacs.3c04679
10.1002/anie.202301892
10.1007/s11426-023-1731-x
10.1021/cr020038p
10.1021/acscatal.9b05011
10.1039/D3QO00126A
10.1021/jacs.1c07562
10.1002/anie.201707862
10.1021/jacs.1c04427
10.1021/acs.accounts.1c00135
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References Majhi J. (ref12/cit12d) 2023; 62
ref6/cit6
ref3/cit3
Guo C.-X. (ref2/cit2b) 2016; 22
ref9/cit9c
ref9/cit9b
ref9/cit9a
ref10/cit10a
ref12/cit12f
ref10/cit10b
ref12/cit12e
ref12/cit12c
ref12/cit12b
ref12/cit12a
ref14/cit14
ref8/cit8
ref5/cit5
ref2/cit2a
ref1/cit1a
ref1/cit1b
ref11/cit11g
ref11/cit11f
ref11/cit11i
ref11/cit11h
ref11/cit11c
ref11/cit11b
ref11/cit11e
ref11/cit11d
ref11/cit11a
ref13/cit13
ref4/cit4
ref7/cit7
References_xml – ident: ref7/cit7
  doi: 10.1038/s41467-018-07351-2
– ident: ref11/cit11b
  doi: 10.31635/ccschem.020.202000374
– ident: ref4/cit4
  doi: 10.1002/asia.201900379
– ident: ref6/cit6
  doi: 10.1002/anie.201806874
– ident: ref11/cit11c
  doi: 10.1016/j.chempr.2021.08.004
– ident: ref11/cit11d
  doi: 10.1038/s41929-022-00841-z
– ident: ref10/cit10a
  doi: 10.1021/acs.orglett.2c01533
– ident: ref12/cit12e
  doi: 10.1021/acscatal.3c04125
– ident: ref11/cit11f
  doi: 10.1016/S1872-2067(23)64468-7
– ident: ref9/cit9a
  doi: 10.1021/acscatal.2c06377
– ident: ref12/cit12f
  doi: 10.1016/j.scib.2023.11.018
– ident: ref8/cit8
  doi: 10.1039/D3GC02955G
– ident: ref11/cit11g
  doi: 10.1007/s11426-022-1554-x
– ident: ref2/cit2a
  doi: 10.1021/acs.orglett.2c01267
– ident: ref12/cit12a
  doi: 10.1021/jacs.0c03144
– ident: ref13/cit13
  doi: 10.1021/j100300a045
– ident: ref1/cit1b
  doi: 10.1021/cr9300348
– volume: 62
  start-page: e202311853
  year: 2023
  ident: ref12/cit12d
  publication-title: Angew. Chem., Int. Ed.
  contributor:
    fullname: Majhi J.
– ident: ref9/cit9b
  doi: 10.1002/cctc.202300695
– ident: ref1/cit1a
  doi: 10.1021/acs.accounts.9b00621
– ident: ref11/cit11e
  doi: 10.1016/S1872-2067(22)64140-8
– volume: 22
  start-page: 17156
  year: 2016
  ident: ref2/cit2b
  publication-title: Chem.-Eur. J.
  doi: 10.1002/chem.201604623
  contributor:
    fullname: Guo C.-X.
– ident: ref14/cit14
  doi: 10.1021/jacs.3c04679
– ident: ref11/cit11h
  doi: 10.1002/anie.202301892
– ident: ref10/cit10b
  doi: 10.1007/s11426-023-1731-x
– ident: ref3/cit3
  doi: 10.1021/cr020038p
– ident: ref5/cit5
  doi: 10.1021/acscatal.9b05011
– ident: ref9/cit9c
  doi: 10.1039/D3QO00126A
– ident: ref12/cit12b
  doi: 10.1021/jacs.1c07562
– ident: ref11/cit11a
  doi: 10.1002/anie.201707862
– ident: ref12/cit12c
  doi: 10.1021/jacs.1c04427
– ident: ref11/cit11i
  doi: 10.1021/acs.accounts.1c00135
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