Diastereoselective auto-protonation of enolates anti-houk selectivity |
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| Institution: | 1. Department of Internal Medical Nursing, Nursing Faculty, Hacettepe University, Ankara, Turkey;2. Dr Abdurrahman Yurtaslan Oncology Training and Research Hospital, Ankara, Turkey;1. College of Land and Environment, Shenyang Agricultural University, Shenyang, Liaoning Province 110866, China;2. Dale Bumpers Small Farms Research Center, Booneville AR72927, USA |
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| Abstract: | 1,4-Addition reaction of lithiated methyl dithioacetate with α,β-disubstituted enones affords 5-oxodithioesters. The diastereoselectivity ranges from moderate to high (> 95:5) in favour of the syn isomer. This anti-Houk selectivity arises from an ‘auto-protonation’, involving transfer of the hydrogen α to the thiocarbonyl group towards the enolate moiety. A pseudo-cyclic transition state leading to the syn product is postulated. |
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