89717-96-4Relevant articles and documents
SIMPLE SYNTHESIS OF &β-SILYLOXYACYLCYCLOPROPANES AND THE HOMOALLYL REARRANGEMENT OF CYCLOPROPYLCARBINOLS BY THE ACTION OF TRIMETHYLSILYL HALIDES IN THE PRESENCE OF ZINC HALIDES
Cheskis, B. A.,Ivanova, N. M.,Moiseenkov, A. M.,Nefedov, O. M.
, p. 1839 - 1849 (1990)
The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave β-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones.Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides.The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.
Enzyme-triggered enantioconvergent transformation of haloalkyl epoxides
Mayer, Sandra F.,Steinreiber, Andreas,Orru, Romano V. A.,Faber, Kurt
, p. 4537 - 4542 (2007/10/03)
Biocatalytic hydrolysis of 2,3-disubstituted rac-cis- and rac-trans-haloalkyl epoxides 1a-8a using the epoxide hydrolase activity of whole bacterial cells furnished the corresponding vicinal diols 1b-8b as intermediates; these (spontaneously) underwent ring closure to yield cyclic products 1c-6c through an enzyme-triggered cascade reaction. In particular, cis-configured substrates (1a, 3a, 5a, 7a) were transformed in an enantioconvergent fashion, which resulted in the formation of single stereoisomeric products in 100% des and up to 92% ees from the racemates.
