4,5-Diisopropyl-B-[(E)-[(3′-menthofuryl)dimethylsilyl]allyl]-1,3,2- dioxaborolane, an Improved Chiral Reagent for the Anti α-Hydroxyallylation of Aldehydes: Application to the Enantioselective Synthesis of (-)-Swainsonine

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1112-1124

  Hunt, J A ^a   Roush, William R ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SWAINSONINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030973907     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961840s     Document Type: Article

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70. 1H NMR analysis) for use in subsequent reactions
71. Diethanolamine complex 17 would not crystallize if larger quantities of diethanolamine were used. The stoichiometry (0.3 equiv of diethanolamine) here is consistent with the efficiency of the preparation of allylboronate 10 directly from allylsilane 15.