A practical synthesis of essentially enantiopure syn-propionate aldols using a chiral oxazaborolidinone-promoted asymmetric aldol reaction coupled with radical reduction

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6447-6449

  Kiyooka, Syun ichi ^a   Shahid, Kazi A ^a   Hena, Mostofa A ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

Asymmetric aldol reaction; Chiral Lewis acid; Diastereoselective radical reduction

Indexed keywords

OXAZABOROLIDINONE; PROPIONATE ALDOL DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHIRALITY; ENANTIOMER; ISOMERISM; POLYMERIZATION; PROMOTER REGION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033609840     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01278-2     Document Type: Article

References (15)

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15. After separation with silica gel flash column chromatography, syn- and anti-3 both showed 98% ee, determined by HPLC with Daicel Chiralcel AD and OD columns. The assignment of syn and anti configurations was confirmed by NOE experiments of the acetonide derivatives obtained after reduction of the ester moiety.