Asymmetric cyanation of activated olefins with ethyl cyanoformate catalyzed by a modular titanium catalyst

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1280-1283

  Wang, Jun ^a   Li, Wei ^a   Liu, Yanling ^a   Chu, Yangyang ^a   Lin, Lili ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a  

^a China   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; ACETONITRILE DERIVATIVE; ALKENE; TITANIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETONITRILES; ALKENES; CATALYSIS; GAMMA-AMINOBUTYRIC ACID; MOLECULAR STRUCTURE; STEREOISOMERISM; TITANIUM;

EID: 77949848412     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100169r     Document Type: Article

References (45)

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40. When TMSCN was used as cyanide source, mono- and di-TMS biphenol were detected by TLC in the reaction mixture. So as the reaction proceeded, the catalyst might be partially decomposed. In contrast, CNCOOEt was much less reactive than TMSCN to react with biphenol. In fact, no ethoxyformate protected biphenol was observed. Therefore, it might be one of the reasons for the fact that CNCOOEt gave better result. Also, it could not be ruled out the possibility that different reaction pathway might go for these two structurally total different cyanide sources.
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44. 4/(R)-or (5)-3,3′-di-2-naphthyl-1,1′-bi-2-naphthol (1/1/1, 10 mol %) as catalyst, olefin 4a (0.1 mmol), CNCOOEt (0.2 mmol), and i-PrOH (0.2 mmol) in toluene (0.2 mL) for 45 h at 0 °C. Product 6a was obtained in 33% yield with 91% ee for (R)-3,3′-di-2-naphthyl-1, 1′-bi-2-naphthol and 23% yield with 85% ee for (5)-enantiomer.
45. α,β-Unsaturated diesters could be prepared in a single step by Knoevenagel condensation of the corresponding aldehydes and diethyl malonate, both of which were very cheap and easily available. In fact, a, β-unsaturated diester has been employed as key intermediate for the largescale synthesis of (5)-(+)-3-isobutyl-GABA (pregabalin). However, due to lack of efficient asymmetric method for the cyanation step, resolution procedures were generally involved in these processes (see: reference 9c and Silverman, R. B. Angew. Chem., Int. Ed. 2008, 47, 3500, and references therein).