Molybdenum-catalyzed allylic substitution in glycals: A CC bond-forming Ferrier-type reaction

…, BP Farn, N Hussain, P Kočovský

Index: Malkov, Andrei V.; Farn, Benjamin P.; Hussain, Nigel; Kocovsky, Pavel Collection of Czechoslovak Chemical Communications, 2001 , vol. 66, # 12 p. 1735 - 1745

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Citation Number: 6

Abstract

Abstract The mild, Lewis-acidic complexes [Mo (CO) 4 Br 2] 2,(MeCN) 2 Mo (CO) 3 (SnCl 3) Cl, and (acac) 2 Mo (OTf) 2 have been found to catalyze the C (1)-specific C-glycosylation reaction of glycal acetates 1-3 with silyl enol ethers 4a-4c and electron-rich aromatics 5a, 5b (PhOMe, PhOH). While silyl enol ethers produce predominantly α-C-glycopyranosides (with 2: 1 to 4: 1 selectivity), aromatics tend to afford mainly β-C-glycopyranosides (2: 1 to 3: 1) ...