Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction

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Title:Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction
Creators:
Malkov, Andrei V.
Farn, Benjamin P.
Hussain, Nigel
Kočovský, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 12, pp. 1735-1745
Uncontrolled Keywords:Lewis acids, Allylic substitutions, <i>C</i>-Glycosides, Stereoselective reactions, Molybdenum complexes, Glycals, Carbohydrates

Abstract

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

Title:Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction
Creators:
Malkov, Andrei V.
Farn, Benjamin P.
Hussain, Nigel
Kočovský, Pavel
Uncontrolled Keywords:Lewis acids, Allylic substitutions, <i>C</i>-Glycosides, Stereoselective reactions, Molybdenum complexes, Glycals, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:66
Number:12
Page Range:pp. 1735-1745
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20011735UNSPECIFIED
ID Code:1891
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Malkov, Andrei V.; Farn, Benjamin P.; Hussain, Nigel; Kočovský, Pavel (2001) Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction. Collection of Czechoslovak Chemical Communications, 66 (12). pp. 1735-1745. ISSN 0010-0765

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