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Volumn 4, Issue 11, 1998, Pages 2154-2161

Internal Lewis acid coordination as a powerful tool to promote highly stereoselective alkylation of α-alkyl-β-hydroxy ketones with Grignard reagents

Author keywords

1,3 diols; Alkylation; Asymmetric synthesis; Chelates; Lewis acids

Indexed keywords

KETONE DERIVATIVE; REAGENT;

EID: 0031772090     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981102)4:11<2154::AID-CHEM2154>3.0.CO;2-O     Document Type: Article
Times cited : (22)

References (72)
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    • note
    • More accurate analytical methods (GC or HPLC) cannot be adopted since products 2 decomposed at the high temperatures necessary for GC, and we were unable to attain sufficient separation of the compounds by HPLC.
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    • note
    • Retroaldolic reaction was observed when nonvolatile products were formed. For example, in the reaction of 1ca with MeMgBr we found about 8% yield of propiophenone among the reaction products, and in the reaction of 1aa with PhMgBr, benzyl alcohol was recovered in about 6% yield from the attack of the Grignard reagent on formaldehyde.
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    • In these cases, if the temperature of the reaction mixture is allowed to rise above - 20 °C, then color of the mixture turns from yellow to dark brown and, after the usual work-up, large amounts of intractable sticky and insoluble products were recovered, which are probably due to polymerization processes.
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    • Eds.: B. M. Trost, I. Fleming, S. L. Schreiber, Pergamon Press, Oxford
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    • note
    • * indicate that diastereomeric compounds are obtained as racemates. We prefer this terminology to avoid the ambiguities that could arise from the use of syn-anti or erythro-threo.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.