Boranes in synthesis - VII. Synthesis of 2-dialkylamino-6,6- dimethylbicyclo[3.1.1]heptan-3-ols from (R)-(+)-nopinone. Chiral auxiliaries for the addition of diethylzinc to aromatic aldehydes

Tetrahedron Asymmetry

Volumn 8, Issue 23, 1997, Pages 3863-3871

  Goralski, Christian T ^a   Chrisman, William ^b   Hasha, Dennis L ^a   Nicholson, Lawrence W ^a   Rudolf, Philip R ^a   Zakett, Donald ^a   Singaram, Bakthan ^b  

^a DOW CHEMICAL COMPANY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 DIALKYLAMINO 6,6 DIMETHYLBICYCLO[3.1.1]HEPTAN 3 OL; ALDEHYDE; AMINE; AMINOALCOHOL; BORANE DERIVATIVE; CYCLOHEXANE; DIETHYLZINC; ENAMINE; HYDROGEN PEROXIDE; KETONE; NOPINONE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 0031452416     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00566-1     Document Type: Article

References (26)

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26. These amino alcohols have a minimum enantiomeric excess (ee) of 92% based on the ee of the starting (R)-(+)-nopinone. It is entirely possible that during the recrystallization process the enantiomeric excess was upgraded. This could not be accurately determined by HPLC analysis using a chiral stationary phase since a racemic mixture was not available to demonstrate the separation of the enantiomers.