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Bender, Trandon A; Dabrowski, Jennifer A; Zhong, Hongyu; Gagné, Michel R
Organic letters, 08/2016, Letnik: 18, Številka: 16Journal Article
A B(C6F5)3-catalyzed method for the selective conversion of unsaturated carbohydrates to cyclopentanes and cyclopropanes is disclosed. Catalyst activation of tertiary silanes generates the ion pair (C6F5)3B–HROSi2 whose components synergistically activate C–O bonds for diastereoselective C–C bond formation. Sila-THF cations are invoked as key intermediates facilitating carbocyclizations. Complex chiral synthons are thereby obtained in a single pot.
