Additions and Corrections - On the Addition of Allytrimethylsilane to Glycal Acetates.

Samuel Danishefsky; James Kerwin, Jr.

doi:10.1021/jo00148a625

Additions and Corrections - On the Addition of Allytrimethylsilane to Glycal Acetates.

The Journal of Organic Chemistry ◽

10.1021/jo00148a625 ◽

1982 ◽

Vol 47 (27) ◽

pp. 5428-5428 ◽

Cited By ~ 4

Author(s):

Samuel Danishefsky ◽

James Kerwin, Jr.

Keyword(s):

Glycal Acetates

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

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20011735 ◽

2001 ◽

Vol 66 (12) ◽

pp. 1735-1745 ◽

Cited By ~ 10

Author(s):

Andrei V. Malkov ◽

Benjamin P. Farn ◽

Nigel Hussain ◽

Pavel Kočovský

Keyword(s):

Allylic Substitution ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Type Reaction ◽

Bond Forming ◽

Glycal Acetates ◽

Glycosylation Reaction

The mild, Lewis-acidic complexes [Mo(CO)4Br2]2, (MeCN)2Mo(CO)3(SnCl3)Cl, and (acac)2Mo(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) in a thermodynamically controlled process.

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