70492-65-8Relevant articles and documents
Pheromone synthesis. Part 243: Synthesis and biological evaluation of (3R,13R,1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata, and its stereoisomers
Mori, Kenji,Tashiro, Takuya,Zhao, Boguang,Suckling, David M.,El-Sayed, Ashraf M.
experimental part, p. 2642 - 2653 (2010/05/18)
All of the four stereoisomers of (1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the female sex pheromone of Clania variegata, were synthesized by employing olefin cross metathesis as the key reaction and starting from (R)- or (S)-2-methyl-1-butanol, (R)- or (S)-citronellal, and (S)-2-methyl-3-pentanol. Their bioassay revealed the (3R,13R,1′S)-isomer as the bioactive one, whose more efficient synthesis was achieved in two different ways by employing Wittig reaction as the key step.
Hydroboartion. 62. Monoisopinocampheylborane, an Excellent Chiral Hydroborating Agent for Trans-Disubstituted and Trisubstituted Alkenes. Evidenece for a Strong Steric Dependence in Such Asymmetric Hydroborations
Brown, Herbert C.,Jadhav, Prabhakar K.,Mandal, Arun K.
, p. 5074 - 5083 (2007/10/02)
Monoisopinocampheylborane (IpcBH2), the first monoalkylborane chiral hydroborating agent, is capable of reacting with olefins of varying stuctural and steric requiments to produce, in most cases, clean dialkylboranes.IpcBH2 achieves the asymmetric hydroboration of trans-disubstituted and trisubstituted olefins with exceptionally high asymmetric induction.The product alcohols, produced by oxidation of the intermediate organoboranes, exhibit enantiomeric purities in the range of 53-100percent ee and reveal the same absolute configuration.Enantiomeric purities of the products increase with increasing steric requirements of the alkyl or phenyl substituent in the trans-disubstituted or trisubstituted alkene.
