107796-97-4Relevant articles and documents
Asymmetric synthesis using diisopropyl tartrate modified (E)- and (Z)-crotylboronates: Preparation of the chiral crotylboronates and reactions with achiral aldehydes
Roush, William R.,Ando, Kaori,Powers, Daniel B.,Palkowitz, Alan D.,Halterman, Ronald L.
, p. 6339 - 6348 (1990)
Diisopropyl tartrate modified (E)- and (Z)-crotylboronates 2 and 3 are easily prepared with very high isomeric purity (≥98% E for 2; ≥99% Z for 3) via the metalation of (E)- and (Z)-2-butene with n-BuLi and KOtBu in THF followed by treatment of the (E)- a
An efficient synthesis of (-)-posticlure: The sex pheromone of Orgyia postica
Fernandes, Rodney A.
, p. 5064 - 5070 (2008/03/18)
An efficient multigram synthesis of (-)-posticlure, the first frans-epoxide sex pheromone found in Orgyia postica, from diethyl L-tartrate is described. The synthesis was completed in seven steps and 27 % overall yield. The synthetic strategy features double-Wittig olefination and a stereoselective one-pot conversion of diol to epoxide as the key steps. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis of the optical antipodes of 4-alkyl-γ-lactones
Thijs, Lambertus,Waanders, Peter P.,Stokkingreef, Edwin H. M.,Zwanenburg, Binne
, p. 332 - 337 (2007/10/02)
Optical antipodes of 4-alkyl-γ-lactones 3 have been prepared by photochemical rearrangement of optically active α,β-epoxy diazomethyl ketones 1 in ethanol to give 4-hydroxy-alkenoates 2, followed by reduction of the alkene bond and subsequent lactonization.The required epoxy diazomethyl ketones 1 were obtained via the following sequence of reactions: alkylation of 2-propyn-1-ol, subsequent reduction to the alkenols 6, Sharpless epoxidation to 2,3-epoxy alcohols 7, oxidation to glycidic esters 8 and finally conversion to diazo ketones 1.The enantiomeric purities range from 84 to 100percent.