Asymmetric Aza-Mannich Reactions of Sulfinimines: Scope and Application to the Total Synthesis of a Bromopyrrole Alkaloid

An asymmetric intermolecular aza variant of the Mannich reaction is reported utilizing chiral sulfinimine anions as the nucleophile and N-sulfonyl aldimines as the electrophilic component. A wide range of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering the condens...

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Veröffentlicht in:	Organic letters 2005-12, Vol.7 (26), p.5905-5907
Hauptverfasser:	Lanter, James C, Chen, Hongfeng, Zhang, Xuqing, Sui, Zhihua
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Aza Compounds - chemistry Catalysis Hydrocarbons, Brominated - chemical synthesis Imines - chemistry Marine Biology Molecular Structure Pyrimidines - chemical synthesis Pyrroles - chemical synthesis Sulfinic Acids - chemistry
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Beschreibung
Zusammenfassung:	An asymmetric intermolecular aza variant of the Mannich reaction is reported utilizing chiral sulfinimine anions as the nucleophile and N-sulfonyl aldimines as the electrophilic component. A wide range of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering the condensation products in good to excellent yield with a high degree of stereocontrol. Application of this methodology to the total synthesis of a natural product is reported.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol0525258