Asymmetric Heck Reaction of (R) 1-tert-Butylsulfinylcyclopentene with Arenediazonium Salts

Julián Priego; Juan Carlos Carretero

doi:10.1055/s-1999-2890

Synlett 1999; 1999(10): 1603-1605
DOI: 10.1055/s-1999-2890

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Asymmetric Heck Reaction of (R) 1-tert-Butylsulfinylcyclopentene with Arenediazonium Salts

Julián Priego^* , Juan Carlos Carretero

^*Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain; Fax 34 913 97 39 66; E-mail: juancarlos.carretero@uam.es

Abstract

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The asymmetric Heck reaction of the readily available (R) 1-tert-butylsulfinyl-1-cyclopentene with a variety of para- and meta-substituted arenediazonium tetrafluoroborates is described. In the presence of Ag₂CO₃ as base, in CH₃CN at rt, the reactions occur in good yields (72-79%) with high diastereoselectivities (de = 82-92%) to afford (3S,SR)-3-aryl-2-tert-butylsulfinyl-1-cyclopentenes as the major adducts. In contrast, poor results were obtained from ortho-substituted arenediazonium salts.

Heck reaction - asymmetric synthesis - sulfoxides - diazoniums salts - chiral cyclopentenes

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