253608-06-9Relevant academic research and scientific papers
A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues
Huang, Pei Qiang,Zheng, Xiao,Li Wang, Shi,Liang Ye, Jian,Ren Jin, Li,Chen, Zhong
, p. 3309 - 3317 (2007/10/03)
Successive treatment of a phenyl thioether derived from (S)-malic acid with n-BuLi, lithium naphthalenide (LN), and electrophiles led to 4-hydroxy- 3-substituted 2-pyrrolidinones in one-pot and in high regio- and diastereoselectivity at C-3. N-Debenzylation of 1-benzyl-4-hydroxy-2- pyrrolidinone using LN afforded naturally occurring (-)-(S)-4-hydroxy-2- pyrrolidinone. (-)-(3S,4S)-4-Hydroxy-3-methyl-2-pyrrolidinone, the lactam form of the γ-amino acid residue found in marine natural products, bistramides, was prepared by the same method.
