Asymmetric α‐Allylation of Glycinate with Switched Chemoselectivity Enabled by Customized Bifunctional Pyridoxal Catalysts

Owing to the strong nucleophilicity of the NH2 group, free‐NH2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl r...

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Published inAngewandte Chemie International Edition Vol. 61; no. 17; pp. e202200850 - n/a
Main Authors Ma, Jiguo, Gao, Bin, Song, Guanshui, Zhang, Ruixin, Wang, Qingfang, Ye, Zi, Chen, Wen‐Wen, Zhao, Baoguo
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.04.2022
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Acetates
Acetic acid
Allyl compounds
Allylic Substitution
Amides
Biomimetic Catalysis
Carbonyl Catalysis
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Esters
Glutamic acid
Intermediates
Organocatalysis
Physical Sciences
Pyridoxal
Science & Technology
Stereoisomerism
Stereoselectivity
Vitamin B6
Vitamin B-6
ACTIVATED ALLYLIC ACETATES
Allylic Substitution
CONJUGATE ADDITION-ELIMINATION
ALDEHYDE CATALYSIS
Organocatalysis
GLUTAMIC-ACID DERIVATIVES
ENANTIOSELECTIVE CONSTRUCTION
Carbonyl Catalysis
BIOMIMETIC TRANSAMINATION
DIPHOSPHINE LIGANDS
AMINO-ACIDS
SYNERGISTIC CU/PD CATALYSIS
BAYLIS-HILLMAN CARBONATES
Biomimetic Catalysis
Vitamin B6
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Abstract Owing to the strong nucleophilicity of the NH2 group, free‐NH2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N‐allylation to α‐C allylation. The reaction formed chiral multisubstituted glutamic acid esters as SN2′–SN2′ products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo‐ and enantiocontrol of the pyridoxal catalysts. A novel bifunctional chiral pyridoxal derivative 1 with a bigger catalytic cavity than that of previous pyridoxal catalysts promoted direct asymmetric α‐C allylation of NH2‐unprotected glycinates with Morita–Baylis–Hillman acetates. In this way, the chemoselectivity for glycinates was switched from intrinsic N‐allylation to α‐C allylation to produce chiral glutamic acid esters with excellent stereoselectivity (up to >20 : 1 dr and 97 % ee).
AbstractList Owing to the strong nucleophilicity of the NH2 group, free-NH2 glycinates react with MBH acetates to usually deliver N-allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N-allylation to α-C allylation. The reaction formed chiral multisubstituted glutamic acid esters as SN 2'-SN 2' products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo- and enantiocontrol of the pyridoxal catalysts.Owing to the strong nucleophilicity of the NH2 group, free-NH2 glycinates react with MBH acetates to usually deliver N-allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N-allylation to α-C allylation. The reaction formed chiral multisubstituted glutamic acid esters as SN 2'-SN 2' products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo- and enantiocontrol of the pyridoxal catalysts.
Owing to the strong nucleophilicity of the NH group, free-NH glycinates react with MBH acetates to usually deliver N-allylated products even in the absence of catalysts. Without protection of the NH group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N-allylation to α-C allylation. The reaction formed chiral multisubstituted glutamic acid esters as S 2'-S 2' products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo- and enantiocontrol of the pyridoxal catalysts.
Owing to the strong nucleophilicity of the NH2 group, free‐NH2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N‐allylation to α‐C allylation. The reaction formed chiral multisubstituted glutamic acid esters as SN2′–SN2′ products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo‐ and enantiocontrol of the pyridoxal catalysts.In memory of Robert H. Grubbs
Owing to the strong nucleophilicity of the NH 2 group, free‐NH 2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence of catalysts. Without protection of the NH 2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N‐allylation to α‐C allylation. The reaction formed chiral multisubstituted glutamic acid esters as S N 2′–S N 2′ products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo‐ and enantiocontrol of the pyridoxal catalysts.
Owing to the strong nucleophilicity of the NH2 group, free-NH2 glycinates react with MBH acetates to usually deliver N-allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N-allylation to alpha-C allylation. The reaction formed chiral multisubstituted glutamic acid esters as S(N)2 '-S(N)2 ' products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo- and enantiocontrol of the pyridoxal catalysts.
Owing to the strong nucleophilicity of the NH2 group, free‐NH2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl ring switched the chemoselectivity of the glycinates from intrinsic N‐allylation to α‐C allylation. The reaction formed chiral multisubstituted glutamic acid esters as SN2′–SN2′ products in good yields with excellent stereoselectivity (up to 86 % yield, >20 : 1 dr, 97 % ee). As compared to pyridoxal catalysts bearing an amide side arm at the C2 position, the pyridoxals in this study have a bigger catalytic cavity to enable effective activation of larger electrophiles, such as MBH acetates and related intermediates. The reaction is proposed to proceed via a cooperative bifunctional catalysis pathway, which accounts for the high level of diastereo‐ and enantiocontrol of the pyridoxal catalysts. A novel bifunctional chiral pyridoxal derivative 1 with a bigger catalytic cavity than that of previous pyridoxal catalysts promoted direct asymmetric α‐C allylation of NH2‐unprotected glycinates with Morita–Baylis–Hillman acetates. In this way, the chemoselectivity for glycinates was switched from intrinsic N‐allylation to α‐C allylation to produce chiral glutamic acid esters with excellent stereoselectivity (up to >20 : 1 dr and 97 % ee).
ArticleNumber 202200850
Author Ma, Jiguo
Zhang, Ruixin
Zhao, Baoguo
Wang, Qingfang
Song, Guanshui
Gao, Bin
Ye, Zi
Chen, Wen‐Wen
Author_xml – sequence: 1
  givenname: Jiguo
  surname: Ma
  fullname: Ma, Jiguo
  organization: Shanghai Normal University
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  givenname: Bin
  surname: Gao
  fullname: Gao, Bin
  organization: Shanghai Normal University
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  givenname: Guanshui
  surname: Song
  fullname: Song, Guanshui
  organization: Shanghai Normal University
– sequence: 4
  givenname: Ruixin
  surname: Zhang
  fullname: Zhang, Ruixin
  organization: Shanghai Normal University
– sequence: 5
  givenname: Qingfang
  surname: Wang
  fullname: Wang, Qingfang
  organization: Shanghai Normal University
– sequence: 6
  givenname: Zi
  surname: Ye
  fullname: Ye, Zi
  organization: Shanghai Normal University
– sequence: 7
  givenname: Wen‐Wen
  orcidid: 0000-0002-2723-2843
  surname: Chen
  fullname: Chen, Wen‐Wen
  email: wenwen@shnu.edu.cn
  organization: Shanghai Normal University
– sequence: 8
  givenname: Baoguo
  orcidid: 0000-0001-7579-6670
  surname: Zhao
  fullname: Zhao, Baoguo
  email: zhaobg2006@shnu.edu.cn
  organization: Shanghai Normal University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/35182094$$D View this record in MEDLINE/PubMed
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ISSN 1433-7851
1521-3773
IngestDate Fri Jul 11 06:44:05 EDT 2025
Fri Jul 25 12:12:28 EDT 2025
Wed Feb 19 02:25:28 EST 2025
Wed Jul 09 18:33:23 EDT 2025
Fri Aug 29 16:02:18 EDT 2025
Thu Apr 24 23:09:42 EDT 2025
Tue Jul 01 01:18:17 EDT 2025
Wed Jan 22 16:25:06 EST 2025
IsPeerReviewed true
IsScholarly true
Issue 17
Keywords Vitamin B-6
ACTIVATED ALLYLIC ACETATES
Allylic Substitution
CONJUGATE ADDITION-ELIMINATION
ALDEHYDE CATALYSIS
Organocatalysis
GLUTAMIC-ACID DERIVATIVES
ENANTIOSELECTIVE CONSTRUCTION
Carbonyl Catalysis
BIOMIMETIC TRANSAMINATION
DIPHOSPHINE LIGANDS
AMINO-ACIDS
SYNERGISTIC CU/PD CATALYSIS
BAYLIS-HILLMAN CARBONATES
Biomimetic Catalysis
Vitamin B6
Language English
License 2022 Wiley-VCH GmbH.
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MergedId FETCHMERGED-LOGICAL-c3730-e795d5bd1fdb4bd63d8953feb4dd953e84bd60cc04e48e0dc95257a86b8b4b593
Notes These authors contributed equally to this work.
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0000-0002-2723-2843
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SSID ssj0028806
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Snippet Owing to the strong nucleophilicity of the NH2 group, free‐NH2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence...
Owing to the strong nucleophilicity of the NH 2 group, free‐NH 2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence...
Owing to the strong nucleophilicity of the NH2 group, free-NH2 glycinates react with MBH acetates to usually deliver N-allylated products even in the absence...
Owing to the strong nucleophilicity of the NH group, free-NH glycinates react with MBH acetates to usually deliver N-allylated products even in the absence of...
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StartPage e202200850
SubjectTerms Acetates
Acetic acid
Allyl compounds
Allylic Substitution
Amides
Biomimetic Catalysis
Carbonyl Catalysis
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Esters
Glutamic acid
Intermediates
Organocatalysis
Physical Sciences
Pyridoxal
Science & Technology
Stereoisomerism
Stereoselectivity
Vitamin B6
Title Asymmetric α‐Allylation of Glycinate with Switched Chemoselectivity Enabled by Customized Bifunctional Pyridoxal Catalysts
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202200850
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https://www.ncbi.nlm.nih.gov/pubmed/35182094
https://www.proquest.com/docview/2649290212
https://www.proquest.com/docview/2630926236
Volume 61
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