A versatile access to vicinal diamine motifs by highly anti-selective asymmetric vinylogous Mannich reactions: an efficient total synthesis of (+)-absouline

文献情報

出版日 2016-03-18

DOI 10.1039/C6QO00022C

インパクトファクター 5.281

著者

Jian-Liang Ye, Hang Chen, Yu-Feng Zhang, Pei-Qiang Huang

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要旨

We report the asymmetric vinylogous Mannich reactions (VMRs) of N-Boc-2-tert-(butyldimethylsilyloxy)pyrrole (TBSOP) with N-tert-butanesulfinylimines. The reaction is highly anti-diastereoselective and shows good generality for the direct construction of a variety of vicinal anti-diamine motifs that are found in a number of biologically active alkaloids and medicinal agents. A VMR adduct was elaborated in six steps into the 1-aminopyrrolizidine alkaloid (+)-absouline, which constitutes the second and also the most efficient total synthesis of the natural enantiomer of the title alkaloid.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

A versatile access to vicinal diamine motifs by highly anti-selective asymmetric vinylogous Mannich reactions: an efficient total synthesis of (+)-absouline

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