Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes

Organic Letters

Volumn 2, Issue 7, 2000, Pages 1001-1004

  Schaus, Scott E ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; EPOXIDE; LANTHANIDE; TRIMETHYLSILYL CYANIDE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; GAS CHROMATOGRAPHY; SYNTHESIS;

CATALYSIS; CHROMATOGRAPHY, GAS; CYANIDES; EPOXY COMPOUNDS; METALS, RARE EARTH; TRIMETHYLSILYL COMPOUNDS;

EID: 0034611489     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005721h     Document Type: Article

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43. Rates were determined by monitoring the appearance of the cyanide ring-opened product 1 as a function of time by GC analysis. An induction period was observed corresponding to the formation of chlorohydrin byproduct. First-order rate constants (pseudo-first-order conditions, 5-fold excess TMSCN, and limiting epoxide) were extracted by plotting In [1] vs time after the induction period was complete (ca. 15% conversion of epoxide) and over > 2 half-lives.