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Synthesis 2002(2): 0232-0236
DOI: 10.1055/s-2002-19798
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot, Four-Component Synthesis of Polyfunctional Sulfones

Xiaogen Huang, Pierre Vogel*
Institut de chimie moléculaire et biologique de l’Ecole Polytechnique Fédérale de Lausanne, Switzerland
Fax: +4(21)6939375; e-Mail: pierre.vogel@epfl.ch;
Further Information

Publication History

Received 6 September 2001
Publication Date:
03 August 2004 (online)

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Abstract

The reaction of (E,E)-1-benzyloxy-2-methylpenta-1,3-diene with trimethylsilyl enol ethers derived from acetone or acetophenone with sulfur dioxide precomplexed with ytterbium triflate or (CF3SO2)2NH generates sulfinate intermediates that can be quenched by a variety of electrophiles to afford the corresponding polyfunctional sulfones in one-pot operations.

Key words

allylation - electron-rich dienes - enoxysilanes - oxyallylation - palladium - sulfinates - sulfones

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14

For examples of multicomponent syntheses, see Ref.13 of preceding report: Bouchez, L.; Vogel, P. Synthesis, preceding paper.