Highly Selective Synthesis of Seven-Membered Azaspiro Compounds by a Rh(I)-Catalyzed Cycloisomerization/Diels-Alder Cascade of 1,5-Bisallenes

被引：13

作者：

Vila, Jordi ^{[1
,2
]}

Sola, Miquel ^{[1
,2
]}

Pla-Quintana, Anna ^{[1
,2
]}

Roglans, Anna ^{[1
,2
]}

机构：

[1] Univ Girona UdG, Fac Ciencies, Inst Quim Computac & Catalisi IQCC, Girona 17003, Catalonia, Spain

[2] Univ Girona UdG, Fac Ciencies, Dept Quim, Girona 17003, Catalonia, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 08期

关键词：

SPIRO; DRUG; PINNATOXINS; TOXINS;

D O I：

10.1021/acs.joc.2c00065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of spiro compounds featuring seven- and six-memberedrings in the spirobicyclic motif is successfully achieved through a cascade processencompassing a rhodium(I)-catalyzed cycloisomerization followed by a highlyselective Diels-Alder homodimerization. The scope of the reaction is analyzed based on a series of synthetic substrates, and control experiments and DFT calculations led us to justify the exquisite degree of selectivity observed

引用

页码：5279 / 5286

页数：8

共 46 条

[1]

Abdul R., 2018, ORG BIOMOL CHEM, V16, P4777

[2]

[Anonymous], 2010, J MED CHEM, V53, P5155

[3] Total Synthesis of Pinnatoxins A and G and Revision of the Mode of Action of Pinnatoxin A [J].