Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with in situ Generated N-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea

Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with in situ Generated N-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea

Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable α-amido sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active α,β-diamino acid...

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Veröffentlicht in:Organic letters 2010-02, Vol.12 (4), p.708-711
Hauptverfasser: Zhang, Haile, Syed, Salahuddin, Barbas, Carlos F
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Catalysis
Cinchona Alkaloids - chemistry
Combinatorial Chemistry Techniques
Glycine - analogs & derivatives
Glycine - chemistry
Imines - chemical synthesis
Imines - chemistry
Models, Molecular
Molecular Structure
Schiff Bases - chemistry
Stereoisomerism
Sulfones - chemistry
Thiourea - chemistry
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Zusammenfassung:Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable α-amido sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active α,β-diamino acid derivatives with up to 99% ee and near-perfect diastereoselection.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902722y