Asymmetric synthesis of 2,4,5-substituted prolines through 1,3-dipolar addition reaction of N-arylidene menthyl esters of alpha-aminoacid with methyl acrylate

Proline and its derivatives constitute the important organic entities as organocatalyst, ACE inhibitors, bioactive molecules/intermediates to bioactive molecules as well as components of various natural products e.g. Kainic acid, (-)-domoic acid, etc. Due to its wide range of utility extensive studi...

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Published inIndian journal of chemistry. Sect. B. Organic chemistry, including medicinal chemistry Vol. 59; no. 7; pp. 1039 - 1042
Main Authors Prasad, Jagdish, Kumar, Munish, Panday, Sharad Kumar
Format Journal Article
LanguageEnglish
Published NEW DELHI Natl Inst Science Communication & Information Resources-Niscair 01.07.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Schiff base
Asymmetric synthesis
X=Y-ZH SYSTEMS
CYCLOADDITIONS
1,3-dipolar addition
CONFIGURATION
alpha-amino acid
2,4,5-substituted prolines
AZOMETHINE YLIDES
POTENTIAL 1,3-DIPOLES
DERIVATIVES
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Abstract Proline and its derivatives constitute the important organic entities as organocatalyst, ACE inhibitors, bioactive molecules/intermediates to bioactive molecules as well as components of various natural products e.g. Kainic acid, (-)-domoic acid, etc. Due to its wide range of utility extensive studies have been made for the synthesis of 2, 3, 4 or 5 substituted prolines. One pot synthesis of 2,4,5-substituted prolines through 1,3-dipolar addition of various amino acids with homochiral acrylate has also been carried out successfully. Herein we wish to report the 1,3-dipolar addition of Schiff bases, where chiral auxiliary has been introduced in the Schiff bases and 1,3dipolar addition with methyl acrylate leading to the synthesis of 2(S),4(S),5(R)-substituted prolines has been achieved successfully.
AbstractList Proline and its derivatives constitute the important organic entities as organocatalyst, ACE inhibitors, bioactive molecules/intermediates to bioactive molecules as well as components of various natural products e.g. Kainic acid, (-)-domoic acid, etc. Due to its wide range of utility extensive studies have been made for the synthesis of 2, 3, 4 or 5 substituted prolines. One pot synthesis of 2,4,5-substituted prolines through 1,3-dipolar addition of various amino acids with homochiral acrylate has also been carried out successfully. Herein we wish to report the 1,3-dipolar addition of Schiff bases, where chiral auxiliary has been introduced in the Schiff bases and 1,3dipolar addition with methyl acrylate leading to the synthesis of 2(S),4(S),5(R)-substituted prolines has been achieved successfully.
Author Panday, Sharad Kumar
Kumar, Munish
Prasad, Jagdish
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  organization: MJP Rohilkhand Univ, Dept Appl Chem, Fac Engn & Technol, Bareilly 243006, Uttar Pradesh, India
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  givenname: Munish
  surname: Kumar
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  givenname: Sharad Kumar
  surname: Panday
  fullname: Panday, Sharad Kumar
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  organization: MJP Rohilkhand Univ, Dept Appl Chem, Fac Engn & Technol, Bareilly 243006, Uttar Pradesh, India
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Cites_doi 10.1021/ja036558z
10.1016/j.tetasy.2011.09.013
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Keywords Schiff base
Asymmetric synthesis
X=Y-ZH SYSTEMS
CYCLOADDITIONS
1,3-dipolar addition
CONFIGURATION
alpha-amino acid
2,4,5-substituted prolines
AZOMETHINE YLIDES
POTENTIAL 1,3-DIPOLES
DERIVATIVES
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PublicationTitle Indian journal of chemistry. Sect. B. Organic chemistry, including medicinal chemistry
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Title Asymmetric synthesis of 2,4,5-substituted prolines through 1,3-dipolar addition reaction of N-arylidene menthyl esters of alpha-aminoacid with methyl acrylate
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