In this work the facial diastereoselectivity of secondary propargylic cations was investigated. Using Bi(OTf)3 as the catalyst, propargylic acetates reacted with different silyl nucleophiles to give the products in high diastereoselectivities. A model was developed to explain the diastereoselectivity of chiral propargylic cations, supported by DFT calculations and low temperature NMR studies. In combination with silyl enol ethers and Bi(OTf)3, tertiary propargylic acetates were shown to form 2 alkenylfurans. Furthermore, benzylic carbocations were generated by oxidation of chiral alkylbenzenes and reacted with nucleophiles in high diastereoselectivities.
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In this work the facial diastereoselectivity of secondary propargylic cations was investigated. Using Bi(OTf)3 as the catalyst, propargylic acetates reacted with different silyl nucleophiles to give the products in high diastereoselectivities. A model was developed to explain the diastereoselectivity of chiral propargylic cations, supported by DFT calculations and low temperature NMR studies. In combination with silyl enol ethers and Bi(OTf)3, tertiary propargylic acetates were shown to form 2 a...
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