1258305-05-3Relevant articles and documents
A stereoselective route to 6-substituted pyrrolo-1,5-benzoxazepinones and their analogues
Brindisi, Margherita,Gemma, Sandra,Alfano, Gloria,Kshirsagar, Giridhar,Novellino, Ettore,Campiani, Giuseppe,Butini, Stefania
, p. 5387 - 5390 (2013/09/12)
We developed a novel and convenient stereoselective path for the preparation of pyrrolo-1,5-benzoxazepinones (PBOs). This innovative route envisaged the employment of (-)-menthol as convenient chiral auxiliary and a key SNAr for the stereoselective preparation of a tertiary aryl-alkyl ether. As a further advancement, we exploited this newly conceived synthetic route for the preparation of 2-substituted PBO analogues to either undergo biological evaluation themselves or give access to a variety of further functionalization options.
Alkaloid induced asymmetric electrocarboxylation of 4-methylpropiophenone
Zhao, Shu-Feng,Zhu, Mei-Xia,Zhang, Kai,Wang, Huan,Lu, Jia-Xing
experimental part, p. 2702 - 2705 (2011/06/19)
The alkaloid-induced electrocarboxylation of 4-methylpropiophenone is examined in mild conditions. Comparative studies with several inductors indicate that the efficient enantiodiscrimination of the electrocarboxylation depends on the nucleophilic quinucl
The stereoselective synthesis of 2-aryl-2-hydroxybutanoic acid via menthyl chiral auxiliaries
Xiang, Ji-Ming,Li, Bao-Lin
experimental part, p. 2015 - 2022 (2010/12/25)
In the presence of titanium(IV) tetraethoxide ((EtO)4Ti), menthyl arylglyoxylates are prepared by transesterification of ethyl arylglyoxylates and natural (-)-(1R,2S,5R)-menthol. Using menthyl as a chiral auxiliary, the corresponding novel (R)-menthyl 2-aryl-2-hydroxybutanoates are synthesized by the addition of Et2Zn with menthyl arylglyoxylates. The structures of the products are characterized by IR and 1H- and 13C-NMR spectroscopy, mass spectrometry, and elemental analysis. The diastereoselectivities are analyzed by HPLC. The addition reactions are completed with good yields and high diastereoisomeric excess (de up to 95%), and, after hydrolysis, the (R)-2-aryl-2-hydroxybutanoic acids are obtained with high optical purities.