Lewis base activation of lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2303-2306

  Denmark, Scott E ^a   Heemstra Jr , John R ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; BASE; BISPHOSPHONIC ACID DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; LEWIS BASE; SILANE DERIVATIVE; SILICON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141853189     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034641l     Document Type: Article

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33. 2 via cannula to a flame-dried bottle with a septum. Between uses, the bottle was stored in a freezer.
34. Although a loading as low as 1 mol % gives near quantitative yields and shows no erosion in enantioselectivity, a catalyst loading of 5 mol % was employed to obtain reasonable rates with more sterically demanding substrates.