15166-68-4Relevant articles and documents
Synthesis of γ-Lactams by Mild, o-Benzoquinone-Induced Oxidation of Pyrrolidines Containing Oxidation-Sensitive Functional Groups
Rong, Hao-Jie,Cheng, Yong-Feng,Liu, Fan-Fan,Ren, Shu-Jian,Qu, Jin
, p. 532 - 540 (2017/04/26)
The late-stage oxidation of substituted pyrrolidines offers good flexibility for the construction of γ-lactam libraries, and especially in recent years the methods for functionalization of pyrrolidine have been available. We reported a new strategy for oxidation of pyrrolidines to γ-lactams: reaction of pyrrolidine with an o-benzoquinone gives an N,O-acetal by direct oxidation of the α-C-H bond of the pyrrolidine ring, and then the N,O-acetal is further oxidized by the o-benzoquinone to the γ-lactam. Because the first oxidation occurs selectively at the α-C-H of the pyrrolidine ring, oxidation-sensitive functional groups (allyl-, vinyl-, hydroxyl-, and amino groups) on pyrrolidine ring are unaffected. The synthetic utility of this novel method was demonstrated by the facile syntheses of (S)-vigabatrin and two analogues.
Chemoenzymatic enantioselective synthesis of 3-hydroxy-2-pyrrolidinones and 3-hydroxy-2-piperidinones
Kamal, Ahmed,Ramana, K. Venkata,Ramana, A. Venkata,Babu, A. Hari
, p. 2587 - 2594 (2007/10/03)
The enantioselective synthesis of 3-hydroxypyrrolidin-2-ones and 3-hydroxy piperidin-2-ones has been carried out in high enantiomeric excess employing immobilized lipase from Pseudomonas cepacia.
