121073-41-4Relevant academic research and scientific papers
Development of C2-Symmetric Chiral Spirocyclic Phase-Transfer Catalysts: Synthesis and Application to Asymmetric Alkylation of Glycinate Schiff Base
Xu, Changming,Qi, Yinsheng,Yang, Xinshuang,Li, Xiangfan,Li, Zhenpeng,Bai, Lei
supporting information, p. 2890 - 2894 (2021/05/05)
A class of C2-symmetric chiral spirocyclic phase-transfer catalysts based on tetramethyl-1,1′-spirobiindane scaffold was synthesized from commercially available bisphenol A in 12 steps with 22-25% total yields, which features a more rigid and stable backb
Atroposelective Phosphoric Acid Catalyzed Three-Component Cascade Reaction: Enantioselective Synthesis of Axially Chiral N-Arylindoles
Wang, Lei,Zhong, Jialing,Lin, Xufeng
supporting information, p. 15824 - 15828 (2019/10/28)
An efficient organocatalytic atroposelective three-component cascade reaction of 2,3-diketoesters, aromatic amines, and 1,3-cyclohexanediones has been developed for the highly enantioselective synthesis of axially chiral N-arylindoles. The success of this method derives from the use of a newly developed second-generation chiral spirocyclic phosphoric acid as the catalyst. In addition, this protocol was extended to the synthesis of an axially chiral monophosphorus ligand.
Resolution of Binaphthols and Spirobiindanols Using Cholesterol Esterase
Kazlauskas, Romas J.
, p. 4953 - 4959 (2007/10/02)
Cholesterol esterase (EC 3.1.1.13) catalyzes the hydrolysis of steroid, binaphthol, and spirobiindanol esters.The hydrolysis of binaphthol and spirobiindanol esters is enantiospecific and can be used to resolve these materials.Simple, synthetic-scale (200 g) procedures are detailed for the resolution of -2,2'-diol (1) and 2,2',3,3'-tetrahydro-3,3,3',3'-tetramethyl-1,1'-spirobi-6,6'-diol (6).Resolution of 1 involved hydrolysis of the dipentanoate ester catalyzed by crude, inexpensive enzyme (bovine pancreas acetone powder) and yielded each enantiomer in > 60percent of theoretical yield with >/= 99percent enantiomeric purity.Similar resolution of 6 by hydrolysis of the dihexanoate ester yielded each enantiomer in > 50percent of theoretical yield with > 95percent enentiomeric purity.These resolution involve two enzymic reactions: hydrolysis of the diester to the monoester followed by hydrolysis of the monoester to the diol.A theoretical analysis of such two-step resolutions suggests that two-step resolutions can yield products with higher enantiomeric purity than can single-step resolutions.
