Enantioselective Synthesis of Tropanes: Bronsted Acid Catalyzed Pseudotransannular Desymmetrization

被引：18

作者：

Rodriguez, Sandra ^{[1
]}

Uria, Uxue ^{[1
]}

Reyes, Efraim ^{[1
]}

Carrillo, Luisa ^{[1
]}

Tejero, Tomas ^{[2
]}

Merino, Pedro ^{[3
]}

Vicario, Jose L. ^{[1
]}

机构：

[1] Univ Basque Country, UPV EHU, Dept Organ Chem 2, POB 644, Bilbao 48080, Spain

[2] Univ Zaragoza, CSIC, ISQCH, E-50009 Zaragoza, Spain

[3] Univ Zaragoza, Inst Biocomp & Fis Sistemas Complejos BIFI, E-50009 Zaragoza, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 17期

关键词：

alkaloids; asymmetric catalysis; bronsted Acids; desymmetrization; organocatalysis; ASYMMETRIC-SYNTHESIS; PHOSPHORIC-ACID; DERIVATIVES; ALKALOIDS; ACTIVATION; ESTERS;

D O I：

10.1002/anie.202000650

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the desymmetrization of the starting material and leads to the direct formation of the 8-azabicyclo[3.2.1]octane scaffold with excellent stereoselectivity. The synthetic applicability of the reaction was demonstrated by the enantioselective synthesis of the two natural products (-)-alpha-tropanol and (+)-ferruginine.

引用

页码：6780 / 6784

页数：5

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