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Synlett 2005(1): 26-41  
DOI: 10.1055/s-2004-836050
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Pauson-Khand Reactions of Alkenyl Sulfones and Alkenyl Sulfoxides: Applications in Asymmetric Synthesis

Marta Rodríguez Rivero, Javier Adrio, Juan Carlos Carretero*
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
Fax: +34(91)4973966; e-Mail: juancarlos.carretero@uam.es;
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Publication History

Received 19 July 2004
Publication Date:
29 November 2004 (online)

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Abstract

Unlike other types of electron-deficient alkenes, alkenyl sulfones and alkenyl sulfoxides are excellent alkene partners in Pauson-Khand reactions (PKR). In the case of the intramolecular PKR of appropriately substituted 1-sulfinyl-1,6-enynes and 1-sulfonyl-3-oxygenated-1,6-enynes novel stereoselective processes and applications in asymmetric synthesis have been developed. Furthermore, using the cobalt-chelating dimethylaminophenyl vinyl sulfoxide as substrate, their intermolecular PKR with terminal alkynes provide the first intermolecular asymmetric version of PKR with non-strained alkenes. The resulting 5-sulfinyl-2-cyclopentenones are versatile intermediates in the enantioselective synthesis of natural cyclopentanoids.

  • 1 Introduction

  • 2 Background: PKR of Electron-Deficient Alkenes

  • 3 Intramolecular PKR of γ-Oxygenated α,β-Unsaturated ­Sulfones and Related Enynes

  • 4 PKR of α,β-Unsaturated Sulfoxides

  • 4.1 Intramolecular Processes

  • 4.2 Intermolecular Processes

  • 4.3 Applications to the Enantioselective Synthesis of Natural Cyclopentanoids

  • 5 Summary

Key words

Pauson-Khand reaction - alkenyl sulfones - alkenyl sulfoxides - asymmetric synthesis - chiral auxiliary - cyclopentanoid synthesis