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Cascade Reactions Involving Pauson–Khand and Related Processes

  • Javier Pérez-CastellsEmail author
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 19)

Abstract

The Pauson–Khand [2 + 2 + 1] cycloaddition is one of the best ways to construct a cyclopentenone. It implies the formation of three new bonds and one or two cycles in the intermolecular or intramolecular versions, respectively. Furthermore some groups have enhanced the synthetic power of this transformation by combining the PKR with other processes. In addition, some unexpected results imply that successive events have occurred, usually after the cycloaddition process. This review aims to point out the most recent advances in cascade reactions in which the Pauson–Khand and PK-type reactions are involved. The non-specialist reader will have an introduction section to outline the state of the art of this chemistry. This will involve, the reaction mechanism, the most useful reaction conditions, the scope of the inter- and intramolecular PKR and the development of asymmetric and catalytic versions.

Catalysis Cycloaddition Cyclopentenones Pauson–Khand reaction Transition metal complexes 

Abbreviations

BINAP

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

BSA

Bis(trimethylsilyl)acetamide

BOC

tert-Butoxycarbonyl

cod

Ciclooctadiene

dba

Dibenzylidenacetone

DCM

Dichloromethane

DME

Dimethoxietane

DMF

N,N-Dimethylformamide

dppe

Bis(diphenylphosphino)ethane

dppp

Bis(diphenylphosphino)propane

DSAC

Dry state adsorption conditions

EWG

Electronic withdrawing group

NMO

4-Methylmorpholine N-oxide

PKR

Pauson–Khand reaction

RCM

Ring-closing metathesis

SDS

Dodecyl sulfate, sodium salt

TBS

terc-Butyldimethylsilyl

TFA

Trifluoroacetic acid

TIPS

Triisopropylsilyl

TMANO

Trimethylamine N-oxide

TolilBINAP

2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl

TON

Turnover number

TPPTS

Triphenylphosphine-3,3′,3′′-trisulfonic acid trisodium salt

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Authors and Affiliations

  1. 1.Dpt. Chemistry, Fac. FarmaciaUniversidad San Pablo CEU.MadridSpain

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