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Volumn 47, Issue 34, 2011, Pages 9621-9623

Hydrogen bonding mediated enantioselective organocatalysis in brine: Significant rate acceleration and enhanced stereoselectivity in enantioselective Michael addition reactions of 1,3-dicarbonyls to β-nitroolefins

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DICARBONYL DERIVATIVE; ACETYLACETONE; ALKENE DERIVATIVE; AMIDE; BETA NITROOLEFIN DERIVATIVE; BRINE; CARBONYL DERIVATIVE; NITROSTYRENE; SOLVENT; SQUARAMIDE; SQUARIC ACID DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

EID: 80051756054     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc13637b     Document Type: Article
Times cited : (100)

References (12)
  • 10
    • 77649329258 scopus 로고    scopus 로고
    • Heterogeneity was crucial for observing large rate acceleration. Thus, the reaction time can be strongly dependent on the efficiency of mixing of the reaction mixture. Thus, we used several magnetic stir bars for efficient mixing and grinding of the solid formed during the reaction. More efficient mixing of the reaction mixture would further shorten the reaction time Other solvents were also screened for the reaction using the catalyst QN-SQA, but the conversion and enantioselectivity were found to be significantly inferior in comparison to those obtained in brine; e.g., DMSO (1 h for 99% conversion, racemic), MeOH (96 h for 99% conversion, 99% ee), see ESI
    • H. Jiang M. W. Paixão D. Monge K. A. Jørgensen J. Am. Chem. Soc. 2010 132 2775 2783
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2775-2783
    • Jiang, H.1    Paixão, M.W.2    Monge, D.3    Jørgensen, K.A.4
  • 11
    • 3242699566 scopus 로고    scopus 로고
    • 2O has a ca. 20% higher viscosity which may make mixing more difficult, and is a better solvent for nonpolar solutes; this must reduce the hydrophobic hydration effect
    • R. Breslow Acc. Chem. Res. 2004 37 471 478
    • (2004) Acc. Chem. Res. , vol.37 , pp. 471-478
    • Breslow, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.