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Synlett 1999; 1999(10): 1603-1605
DOI: 10.1055/s-1999-2890
DOI: 10.1055/s-1999-2890
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Asymmetric Heck Reaction of (R) 1-tert-Butylsulfinylcyclopentene with Arenediazonium Salts
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Publication Date:
31 December 1999 (online)
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