Asymmetric homologation of boronic esters bearing azido and silyloxy substituents

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6650-6653

  Singh, Rajendra Prasad ^a   Matteson, Donald S ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; AZIDE; BORON; CARBON; DICHLOROMETHANE; ESTER; LITHIUM DERIVATIVE; NITROGEN; NITROMETHANE; OXYGEN; SODIUM AZIDE; SOLVENT; TETRABUTYLAMMONIUM; WATER;

ARTICLE; CATALYST; CHEMICAL BOND; HYDROLYSIS; METAL BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

AZIDES; BORONIC ACIDS; ESTERS; ORGANOSILICON COMPOUNDS;

EID: 0034613281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo005522b     Document Type: Article

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21. The air oxidation hypothesis cannot be proved with the present data, but in an ongoing investigation of closely analogous chemistry involving multistep synthesis, NMR evidence of autoxidation of samples during storage has been observed, and careful protection of all intermediates from air exposure during storage has resulted in significantly improved yields in later stages of the synthesis. The tert-butyldiphenylsilyl protecting group has consistently given excellent results. Matteson, D. S.; Pharazyn, P. S. Unpublished results.