344765-03-3Relevant articles and documents
Highly efficient enantioselective synthesis of 1,3-disubstituted 2,5-diketopiperazine derivatives via microwave irradiation
Han, Si Yeon,Gong, Young-Dae
supporting information, p. 3426 - 3434 (2019/11/03)
Chiral 2,5-diketopiperazine (2,5-DKP) derivatives have a broad range of biological activities in the medicinal field. The synthetic protocols of 1,3-disubstituted 2,5-DKPs via base-catalyzed cyclization of chloroacetamide have been reported. However, there are several drawbacks, such as an overly long reaction time, low to moderate yield, and racemization of the products. The sequence modified herein of 1,3-disubstituted 2,5-DKPs involves microwave-assisted cyclization. It increases yields and reduces reaction time. Furthermore, employing N-PMB protection prevents racemization, which frequently occurs in the base-catalyzed cyclization reaction. Consequently, the rapid synthetic method of enantiomerically pure 1,3-disubstituted 2,5-DKPs via microwave reaction was established successfully.
Mild construction of 3-methyl tetramic acids enabling a formal synthesis of palau'imide
Bai, Wen-Ju,Jackson, Stephen K.,Pettus, Thomas R. R.
, p. 3862 - 3865 (2012/09/22)
A general method to construct 3-methyl-4-O-methylated tetramic acids displaying a C-5 stereocenter is presented. The synthetic sequence employs a SmI2-mediated cyclization, whereby the chirality of the emerging tetramic acid core is retained from the starting chiral amino acid. Application to palau'imide is discussed.
Dynamic diastereoselectivity during iron carbonyl mediated spirocyclization reactions
Pearson, Anthony J.,Sun, Huikai,Wang, Xiaolong
, p. 2547 - 2557 (2007/10/03)
Dynamic diastereoselectivity during Fe(CO)3 promoted [6 + 2] ene spirocyclization of 35a and 35b, having a chiral center on the pendent side chain, was investigated and gave rise to products 28a and 28b instead of four possible isomers. From th