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Volumn 121, Issue 11, 1999, Pages 2460-2470

Asymmetric memory at labile, stereogenic boron: Enolate alkylation of oxazaborolidinones

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; ALCOHOL DERIVATIVE; ALLYL BROMIDE; BENZYL BROMIDE; BORON; BORON DERIVATIVE; ENOLATE; METHYL IODIDE; NAPHTHYL GROUP; OXAZABOROLIDINONE DERIVATIVE; PHENYLALANINE; PHENYLGLYCINE; UNCLASSIFIED DRUG; VALINE;

EID: 0033599496     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983555r     Document Type: Article
Times cited : (149)

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    • note
    • 1H NMR that is now understood to indicate a 1:2 mixture of ent-44: [ent-45 + 45]. The more stable oxazaborolidine fraction (trans B-phenyl and C-phenyl) was separated by chromatography, hydrolyzed to 46 (methanol, reflux) followed by ethylenediamine, and derivatized with (S)-2-chloropropionyl chloride. This produced a ca. 4:1 mixture of (S,R):(S,S) N-(α-chloropropionyl)-α-methylphenylglycine diastereomers, identified by chemical shift comparison with the authentic isomers reported by Kellogg et al. (ref 11). The initial ratio of alkylation products ent-44:[ent-45 + 45] is consistent with the observed diastereomer ratio if ca. 20-30% of the original ent-44 had isomerized to 45.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.