Application of rhodium complexes of chiral diphenyl-phosphino-functionalized N-heterocyclic carbenes as catalysts in enantioselective conjugate additions of arylboronic acids

The Rh complex 1a of (S,S)-1-(2-diphenylphosphanyinaphthalen-1-yl)-3-(2-isopropylphenyl)- 4,5-diphenylimidazolidin-2-ylidene was found to promote enantioselective conjugate additions of aryl-boronic acids to enones and alpha,beta-unsaturated esters with up to 98% yield and > 99% ee. Products of t...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 347; no. 11-13; pp. 1495 - 1498
Main Authors Becht, JM, Bappert, E, Helmchen, G
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.10.2005
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
chiral N-heterocyclic carbenes
BACLOFEN
REAGENTS
TRANSITION-METAL-COMPLEXES
ASYMMETRIC 1,4-ADDITION
LIGANDS
RH
asymmetric catalysis
conjugate addition
boronic acids
rhodium
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Summary:The Rh complex 1a of (S,S)-1-(2-diphenylphosphanyinaphthalen-1-yl)-3-(2-isopropylphenyl)- 4,5-diphenylimidazolidin-2-ylidene was found to promote enantioselective conjugate additions of aryl-boronic acids to enones and alpha,beta-unsaturated esters with up to 98% yield and > 99% ee. Products of the latter reaction can be transformed into GABA antagonists.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200404327