From Cyclopropene to Housane Derivatives Via Intramolecular Cyclopropanation

被引：2

作者：

Coto, Dario ^{[1
,2
,3
]}

Suarez-Garcia, David ^{[1
,2
,3
]}

Mata, Sergio ^{[1
]}

Fernandez, Israel ^{[3
,4
]}

Lopez, Luis A. ^{[1
,2
,3
]}

Vicente, Ruben ^{[1
,2
,3
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, Julian Claveria 8, Oviedo 33006, Spain

[2] Univ Oviedo, Inst Univ Quim Organometal Enrique Mol, Oviedo 33006, Spain

[3] Ctr Innovac Quim Avanzada ORFEO CINQA, Oviedo, Spain

[4] Univ Complutense Madrid, Dept Quim Organ, Ciudad Univ, Madrid 28040, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2024年 / 63卷 / 46期

关键词：

cyclopropenes; housanes; terpenes; strained compounds; CYCLOADDITION REACTIONS; CATALYZED-REACTIONS; RING-SYSTEMS; BICYCLO<2.1.0>PENTANE; CYCLOISOMERIZATION; STEREOCHEMISTRY; ISOMERIZATIONS; CHEMISTRY; KINETICS; ALKENES;

D O I：

10.1002/anie.202409226

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of housane derivatives from cyclopropenes is described. Under rhodium(II) catalysis, cyclopropenylvinyl carbinols can regioselectively generate a carbene intermediate which undergoes an intramolecular cyclopropanation to form a housane, a skeleton with similar ring strain as the cyclopropene precursor. The procedure shows a remarkable broad scope and efficiency. Moreover, the method served to prepare man-made housane-containing terpene derivatives, which are not accessible by Nature.

引用

页数：6

共 71 条

[1] ELECTRONIC SUBSTITUENT EFFECTS ON THE ACID-CATALYZED [4(+)+2] CYCLOADDITION OF ISOPYRAZOLES WITH CYCLOPENTADIENE AND THE PHOTOCHEMICAL AND THERMAL DENITROGENATION OF THE RESULTING 1,4-DIARYL-7,7-DIMETHYL-2,3-DIAZABICYCLO[2.2.1]HEPT-2-ENE AZOALKANES TO BICYCLO[2.1.0]PENTANES [J].

ADAM, W ;

HARRER, HM ;

NAU, WM ;

PETERS, K .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3786-3797

[2]

[Anonymous], 2019, Angew. Chem

[3]

[Anonymous], 1974, Angew. Chem. Int. Ed. Engl, V13, P466

[4]

[Anonymous], 2019, Angew. Chem. Int. Ed, V58, P1724

[5]

[Anonymous], 2015, Angew. Chem. Int. Ed, V54, P12139

[6]

[Anonymous], 2022, Angew. Chem. Int. Ed, V61

[7]

[Anonymous], 2012, Angew. Chem. Int. Ed, V51, P1124

[8]

[Anonymous], 2011, Angew. Chem. Int. Ed, V50, P5932

[9]

Anslyn E. V., 2005, Modern Physical Organic Chemistry, P110

[10]

Baker R J, 2022, Angew. Chem.., V134

← 1 2 3 4 5 6 7 8 →