FAM‐Ag‐catalyzed asymmetric synthesis of heteroaryl‐substituted pyrrolidines
New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl...
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| Published in | Chirality (New York, N.Y.) Vol. 33; no. 8; pp. 465 - 478 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl‐substituted pyrrolidines by the 1,3‐dipolar cycloaddition (1,3‐DC) reaction of azomethine ylides. 2‐Thienyl, 2‐furyl, 2‐, 3‐, and 4‐pyridyl aldimines were prepared and used with N‐methylmaleimide, dimethyl maleate, tert‐butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl‐substituted pyrrolidines. 1,3‐DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single‐crystal X‐ray analysis.
New FAM ligands were synthesized and used as chiral catalysts for the asymmetric synthesis of heteroaryl‐substituted pyrrolidines. |
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| AbstractList | Abstract
New derivatives of
FAM
(ferrocenyl aziridinyl methanol) ligands
NFAM1–4
(naphthyl ferrocenyl aziridinyl methanol) and
CFAM1–4
(cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl‐substituted pyrrolidines by the 1,3‐dipolar cycloaddition (1,3‐DC) reaction of azomethine ylides. 2‐Thienyl, 2‐furyl, 2‐, 3‐, and 4‐pyridyl aldimines were prepared and used with
N
‐methylmaleimide, dimethyl maleate,
tert
‐butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl‐substituted pyrrolidines. 1,3‐DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands
NFAM1–4
and
CFAM1–4
were fully characterized, and their absolute stereochemistry was determined by single‐crystal X‐ray analysis. New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl‐substituted pyrrolidines by the 1,3‐dipolar cycloaddition (1,3‐DC) reaction of azomethine ylides. 2‐Thienyl, 2‐furyl, 2‐, 3‐, and 4‐pyridyl aldimines were prepared and used with N‐methylmaleimide, dimethyl maleate, tert‐butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl‐substituted pyrrolidines. 1,3‐DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single‐crystal X‐ray analysis. New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl‐substituted pyrrolidines by the 1,3‐dipolar cycloaddition (1,3‐DC) reaction of azomethine ylides. 2‐Thienyl, 2‐furyl, 2‐, 3‐, and 4‐pyridyl aldimines were prepared and used with N‐methylmaleimide, dimethyl maleate, tert‐butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl‐substituted pyrrolidines. 1,3‐DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single‐crystal X‐ray analysis. New FAM ligands were synthesized and used as chiral catalysts for the asymmetric synthesis of heteroaryl‐substituted pyrrolidines. |
| Author | Dogan, Özdemir Araz, Mihrimah Beksultanova, Nurzhan Bulut, Merve Polat‐Çakır, Sıdıka Gözükara, Zeynep Aygün, Muhittin |
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| Keywords | substituted pyrrolidines asymmetric synthesis SELF-DISPROPORTIONATION ENANTIOMERS AZOMETHINE YLIDES chiral metal catalyst chiral FAM ligands heteroaryl‐ DERIVATIVES ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION |
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| Notes | Funding information Middle East Technical University; Scientific and Technological Research Council of Turkey, Grant/Award Number: 118Z414 Dedicated to Professor Philip P. Garner on the occasion of his 66th birthday. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Snippet | New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl... New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1-4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1-4 (cyclohexyl ferrocenyl aziridinyl... Abstract New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl... |
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| SubjectTerms | Acrylics Acrylonitrile Asymmetric synthesis Asymmetry Catalysts Chemical synthesis Chemistry Chemistry, Analytical Chemistry, Medicinal Chemistry, Organic chiral FAM ligands chiral metal catalyst Crystallization Cycloaddition heteroaryl‐substituted pyrrolidines Life Sciences & Biomedicine Ligands Methanol Pharmacology & Pharmacy Physical Sciences Science & Technology Stereochemistry Substitutes |
| Title | FAM‐Ag‐catalyzed asymmetric synthesis of heteroaryl‐substituted pyrrolidines |
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