Asymmetric Vinylogous Mannich Reactions: A Versatile Approach to Functionalized Heterocycles

Asymmetric Vinylogous Mannich Reactions: A Versatile Approach to Functionalized Heterocycles

Asymmetric vinylogous Mannich reaction (VMR) of 2-(tert-butyldimethylsilyloxy)furan (TBSOF, 1) with (R S )- or (S S )-t-BS-imines (3) furnished 5-aminoalkylbutenolides 7a–k in 75–87% yields with anti/syn ratios ranging from 75:25 to 97:3. Butenolides 7a–f,k were readily converted into substituted la...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2011-09, Vol.13 (18), p.4938-4941
Hauptverfasser: Ruan, Shu-Tang, Luo, Jie-Min, Du, Yu, Huang, Pei-Qiang
Format: Artikel
Sprache:eng
Schlagworte:
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
Stereoisomerism
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Asymmetric vinylogous Mannich reaction (VMR) of 2-(tert-butyldimethylsilyloxy)furan (TBSOF, 1) with (R S )- or (S S )-t-BS-imines (3) furnished 5-aminoalkylbutenolides 7a–k in 75–87% yields with anti/syn ratios ranging from 75:25 to 97:3. Butenolides 7a–f,k were readily converted into substituted lactones 8 and 5 and 6-substituted 5-hydroxypiperidin-2-ones 11a–g, which are, in turn, key intermediates for the synthesis of many bioactive compounds.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2020384