124338-53-0Relevant articles and documents
Asymmetric Induction by a Nitrogen14N/15N Isotopomer in Conjunction with Asymmetric Autocatalysis
Matsumoto, Arimasa,Ozaki, Hanae,Harada, Shunya,Tada, Kyohei,Ayugase, Tomohiro,Ozawa, Hitomi,Kawasaki, Tsuneomi,Soai, Kenso
, p. 15246 - 15249 (2016/12/03)
Chirality arising from isotope substitution, especially with atoms heavier than the hydrogen isotopes, is usually not considered a source of chirality in a chemical reaction. An N2,N2,N3,N3-tetramethyl-2,3-butan
Reductive cleavage of acetals and ketals with 9-borabicyclo[3.3.1]nonane
Soderquist, John A.,Kock, Iveliz,Estrella, Maria E.
supporting information, p. 1076 - 1079 (2012/12/23)
The reductive cleavage of benzaldehyde acetals and acetophenone ketals with the air-stable crystalline 9-borabicyclo[3.3.1]-nonane dimer provides monobenzylated ether derivatives of diols and 1,2-oxygen-transposed β-phenethyl alcohols, respectively. The boron moiety is effectively recovered through simple procedures which involve convenient air-stable reagents and boron byproducts. The process is particularly selective for 1,3-diols giving the more substituted monobenzyl ether derivatives exclusively. With acetophenone ketals both reduction and elimination occur, permitting 9-BBN-H to hydroborate the resulting styrene to produce 1,2-oxygen-transposed β-phenethyl alcohols cleanly. Potential applications of this new process were illustrated with the synthesis of the hallucinogen, mescaline, and the analgesic, ibufenac.
Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base
Studer, Martin,Blaser, Hans-Ulrich,Burkhardt, Stephan
, p. 511 - 515 (2007/10/03)
The first successful example of the asymmetric hydrogenation of substituted α-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of >80% were obtained at >95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.