663174-57-0Relevant academic research and scientific papers
N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: Asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B
Ye, Zhao-Bao,Chen, Jie,Meng, Wei-Hua,Huang, Pei-Qiang
experimental part, p. 895 - 902 (2010/08/05)
O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy- pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as β-hydroxy γ-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C.
A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds
Wu, Shao-Feng,Zheng, Xiao,Ruan, Yuan-Ping,Huang, Pei-Qiang
experimental part, p. 2967 - 2975 (2011/02/25)
A flexible diastereoselective approach to trans-(3S)-hydroxyprolinol derivatives is described, which is based on the samarium diiodide-mediated reductive coupling of the chiral 1-pyrroline N-oxide (nitrone)(S)-10 with carbonyl compounds. The reductive hyd
