A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues
PQ Huang, X Zheng, SL Wang, JL Ye, LR Jin…
Index: Huang, Pei Qiang; Zheng, Xiao; Li Wang, Shi; Liang Ye, Jian; Ren Jin, Li; Chen, Zhong Tetrahedron Asymmetry, 1999 , vol. 10, # 17 p. 3309 - 3317
Full Text: HTML
Citation Number: 41
Abstract
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 ...
Related Articles:
Stereoselective synthesis of (S)-oxiracetam and (S)-GABOB from (R)-glyceraldehyde acetonide
[Tetrahedron Letters, , vol. 54, # 21 p. 2637 - 2640]
A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues
[Tetrahedron Asymmetry, , vol. 10, # 17 p. 3309 - 3317]
[Organic Letters, , vol. 2, # 24 p. 3949 - 3952]
A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues
[Tetrahedron Asymmetry, , vol. 10, # 17 p. 3309 - 3317]
A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues
[Tetrahedron Asymmetry, , vol. 10, # 17 p. 3309 - 3317]