132917-66-9Relevant academic research and scientific papers
Lewis-acid catalyzed N-acyliminium ion cyclodimerization: Synthesis of symmetrical 1,4-dioxanes
Ali, Bakhat,Zukerman-Schpector, Julio,Ferreira, Fernando P.,Shamim, Anwar,Pimenta, Daniel C.,Stefani, Hélio A.
, p. 1153 - 1158 (2015/02/19)
The cyclodimerization reaction of N-substituted-5-hydroxy-pyrrolydinones promoted by BF3·Et2O and HCl to obtain symmetrical 1,4-dioxane derivatives was achieved in moderate to good yields, mild conditions, and short reaction times. These transformations render a promising alternative route that provides access to diverse 1,4-dioxane derivatives with a wide structural diversity.
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.
Studies towards the synthesis of (+)-ptilomycalin A; stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams
Louwrier, Saskia,Ostendorf, Martin,Boom, Arnoud,Hiemstra, Henk,Speckamp, W. Nico
, p. 2603 - 2628 (2007/10/03)
Highly stereoselective N-acyliminium ion coupling reactions of β-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.
SYNTHESIS OF STATINE FROM (S)-MALIC ACID; STEREOCONTROL VIA RADICAL CYCLIZATION
Koot, Wim-Jan,Ginkel, Roel van,Kranenburg, Mirko,Hiemstra, Henk,Louwrier, Saskia,et al.
, p. 401 - 404 (2007/10/02)
Highly stereoselective syntheses of enantiomerically pure γ-amino acids statine and 4-epi-statine from (S)-malic acid are described by using, respectively, an intramolecular α-acylamino radical reaction and an intermolecular N-acyliminium allylsilane coupling.
