Syn -selective catalytic asymmetric 1,4-addition of α-ketoanilides to nitroalkenes under dinuclear nickel catalysis

Organic Letters

Volumn 12, Issue 14, 2010, Pages 3246-3249

  Xu, Yingjie ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ANILIDE; NICKEL;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

ALKENES; ANILIDES; CATALYSIS; NICKEL; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77954545346     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101185p     Document Type: Article

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47. 2- 1b complexes does not show any peaks, suggesting that at least one of the Ni metal centers has non-planar coordination mode. On the basis of the molecular model, we assume that the outer Ni center has cis -β configuration due to strain of the bimetallic complexes. In other words, one of the Ni-O bonds of the outer Ni center is speculated to be in apical position. Thus, the Ni-O bond would work as a Brønsted base to deprotonate α-ketoanilide to give the Ni-enolate intermediate. Of course, the proposed mechanism in Figure 3 is too much speculative at the moment, and mechanistic studies, including trials to elucidate precise coordination modes of two Ni metal centers by X-ray single crystal analysis, are ongoing. For the utility of cis -β metal complexes of salens in asymmetric catalysis, see a review: Katsuki, T. Chem. Soc. Rev. 2004, 33, 437