187091-67-4Relevant academic research and scientific papers
General entry to asymmetric one-pot [ N + 2 + n ] cyclization for the synthesis of three- to seven-membered azacycloalkanes
Harada, Shingo,Sakai, Takeo,Takasu, Kiyosei,Yamada, Ken-Ichi,Yamamoto, Yasutomo,Tomioka, Kiyoshi
, p. 7212 - 7222 (2012/11/07)
Enantio- and diastereoselective one-pot synthesis of three- to seven-membered cis-azaheterocycles was achieved using a triggered asymmetric conjugate addition reaction of lithium amide with an enoate, followed by alkylation of the resulting lithium enolat
Heterobimetallic transition metal/rare earth metal bifunctional catalysis: A Cu/Sm/schiff base complex for Syn -selective catalytic asymmetric nitro-mannich reaction
Handa, Shinya,Gnanadesikan, Vijay,Matsunaga, Shigeki,Shibasaki, Masakatsu
supporting information; experimental part, p. 4925 - 4934 (2010/06/18)
The full details of a catalytic asymmetric syn-selective nitro-Mannich reaction promoted by heterobimetallic Cu/Sm/dinucleating Schiff base complexes are described, demonstrating the effectiveness of the heterobimetallic transition metal/rare earth metal bifunctional catalysis. The first-generation system prepared from Cu(OAc)2/Sm(O-iPr)3/Schiff base 1a = 1:1:1 with an achiral phenol additive was partially successful for achieving the syn-selective catalytic asymmetric nitro-Mannich reaction. The substrate scope and limitations of the first-generation system remained problematic. After mechanistic studies on the catalyst prepared from Sm(O-iPr)3, we reoptimized the catalyst preparation method, and a catalyst derived from Sm 5O(O-iPr)13 showed broader substrate generality as well as higher reactivity and stereoselectivity compared to Sm(O-iPr)3. The optimal system with Sm5O(O-iPr)13 was applicable to various aromatic, heteroaromatic, and isomerizable aliphatic N-Boc imines, giving products in 66-99% ee and syn/anti = >20:1-13:1. Catalytic asymmetric synthesis of nemonapride is also demonstrated using the catalyst derived from Sm5O(O-iPr)13.
3-Aminopyrrolidines from α-aminoacids: Total synthesis of (+)-nemonapride from D-alanine
Cam, Thuy Hoang,Viet, Hoang Nguyen,Alezra, Valerie,Kouklovsky, Cyrille
, p. 1162 - 1164 (2008/09/18)
(Chemical Equation Presented) The antipsychotic compound nemonapride 1 was synthesized in nine steps from D-alanine 2. The key steps for the synthesis of the 3-aminopyrrolidine moiety include a Birch reduction of a cyclic enaminoester and the reduction of a pyrrolidinone to the pyrrolidine 7. Final coupling with the benzoic acid derivative 9 gave 1 as a single enantio- and diastereomer.
An easy access to protected (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates
Huang, Pei Qiang,Wang, Shi Li,Ye, Jian Liang,Ruan, Yuan Ping,Huang, You Qing,Zheng, Hong,Gao, Jing Xing
, p. 12547 - 12560 (2007/10/03)
A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2- pyrrolidinones is described. The key steps involve a regioselective Grignard reagent addition to (S)-malimides, and diastereoselective reductive dehydroxylation of the resulting hemi-azaketals. The flexibility of this methodology has been demonstrated by the synthesis of (2R, 3R)-3-amino-1- benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, and the unnatural enantiomer of the β-hydroxy-γ-amino acid residue of hapalosin in lactam form.
First asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine via a highly diastereoselective reductive alkylation
Huang, Pei Qiang,Wang, Si Li,Zheng, Hong,Fei, Xiang Su
, p. 271 - 272 (2007/10/03)
The first asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, from (S)-malic acid was achieved via a highly diastereoselective reductive alkylation.
