Trapping the π-Allylpalladium Intermediate from Fulvene-Derived Azabicyclic Olefin with Soft Nucleophiles

被引：15

作者：

Rajan, Rani ^{[1
]}

John, Jubi ^{[1
]}

Thulasi, Sreeja ^{[1
]}

Joseph, Nayana ^{[1
]}

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

Sawant, R. C. ^{[1
]}

机构：

[1] CSIR, NIIST, Organ Chem Sect, Chem Sci & Technol Div, Trivandrum 695019, Kerala, India

来源：

SYNTHESIS-STUTTGART | 2010年 / 21期

关键词：

azabicyclic olefin; palladium; soft nucleophile; alkylidenecyclopentene; substituted cyclopentanone; 2-hydrazinofulvene; ENANTIOSELECTIVE TOTAL-SYNTHESIS; PALLADIUM-CATALYZED REACTIONS; FISCHER CARBENE COMPLEXES; BICYCLIC HYDRAZINES; STEREOSELECTIVE-SYNTHESIS; ALKYLIDENE CYCLOPENTENES; FACILE SYNTHESIS; DERIVATIVES; REAGENTS; 2-ACETOXYMETHYL-3-ALLYLTRIMETHYLSILANE;

D O I：

10.1055/s-0030-1258227

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile method for the synthesis of a new class of disubstituted alkylidenecyclopentenes has been introduced. The methodology involves the palladium-catalyzed ring opening of pentafulvene-derived bicyclic hydrazines with phenols and active methylene compounds, furnishing 1,4-disubstituted alkylidenecyclopentenes in good yield. The utility of multiple points of functionalization was effectively demonstrated by the synthesis of a substituted cyclopentanone and 2-hydrazinofulvene.

引用

页码：3649 / 3656

页数：8

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