233277-24-2Relevant articles and documents
A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides
Huang, Zhongxing,Low, Kam-Hung,Zhang, Suihan,Zheng, Yin,Zi, Weiwei
, p. 1951 - 1961 (2022/02/09)
Enantioenriched tertiary alkyl halides are prevalent in bioactive molecules and can serve as versatile synthetic intermediates to construct complex structures. While conventional access to these motifs often hinges on stereoselective carbon-halogen or carbon-carbon bond formation reactions, desymmetric approaches using halogenated and prochiral tetrasubstituted carbons are largely elusive in comparison. Here, we report that a suite of dinuclear zinc catalysts with a prolinol- or pipecolinol-derived tetradentate ligand can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-β-hydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access to natural products containing tertiary alcohol motifs.
Lipase mediated preparation of differently protected homochiral 2-aryl- 2-fluoro-1,3-propanediols
Guanti, Giuseppe,Narisano, Enrica,Riva, Renata
, p. 1859 - 1862 (2007/10/03)
Lipase mediated asymmetric monohydrolysis of 2-aryl-2-fluoromalonic acid diesters or monoacetylation of 2-aryl-2-fluoro-1,3-propanediols affords chiral fiuorinated polyfunctionalized C3 synthons in excellent enantiomeric excess and acceptable chemical yields.
