Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols

被引：11

作者：

Chand, S. Sarath ^{[1
,2
]}

Saranya, S. ^{[2
]}

Preethanuj, P. ^{[2
]}

Dhanya, B. P. ^{[1
,2
]}

Jijy, E. ^{[2
]}

Prakash, Praveen ^{[2
]}

Sasidhar, B. S. ^{[1
,2
]}

Szymoniak, Jan ^{[3
]}

Santhini, P. V. ^{[1
,2
]}

Radhakrishnan, K. V. ^{[1
,2
]}

机构：

[1] Acad Sci & Innovat Res AcSIR, New Delhi 110001, India

[2] Natl Inst Interdisciplinary Sci & Technol CSIR, Organ Chem Sect, Trivandrum 695019, Kerala, India

[3] Univ Reims, F-51687 Reims 2, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 19期

关键词：

MESO-BICYCLIC HYDRAZINES; PALLADIUM-CATALYZED REACTIONS; ONE-POT STRATEGY; STEREOSELECTIVE-SYNTHESIS; DIAZABICYCLIC ALKENES; AZABICYCLIC OLEFINS; FACILE SYNTHESIS; ENANTIOSELECTIVE DESYMMETRIZATION; ALKYLIDENE CYCLOPENTENES; CYCLOADDITION REACTIONS;

D O I：

10.1039/c4ob00031e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe our efforts on the Lewis acid catalyzed stereoselective ring-opening of pentafulvene derived diazabicyclic olefins using various ortho-functionalized aryl iodides such as 2-iodoanilines, 2-iodophenols and 2-iodobenzene thiols to access trans-1,2 disubstituted alkylidenecyclopentenes. The scope of the reaction was also explored with a range of easily available aromatic and aliphatic alcohols. Furthermore, the palladium catalyzed intramolecular Heck cyclization of trans-1,2 disubstituted alkylidenecyclopentenes would provide an easy approach for the synthesis of highly functionalized spiropentacyclic frameworks consisting of a cyclopentene fused to an indoline/benzothiophene and pyrazolidine.

引用

页码：3045 / 3061

页数：17

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