890043-61-5Relevant articles and documents
The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: Enantioselective synthesis of β-amino acids
Song, Jun,Wang, Yi,Deng, Li
, p. 6048 - 6049 (2006)
We describe the first efficient, direct asymmetric Mannich reactions with malonates and N-Boc aryl and alkyl imines by cooperative hydrogen-bonding catalysis with a cinchona alkaloid bearing a thiourea functionality. We have also extended the scope of thi
Asymmetric Mannich Reaction and Construction of Axially Chiral Sulfone-Containing Styrenes in One Pot from α-Amido Sulfones Based on the Waste-Reuse Strategy
Li, Dongmei,Tan, Yu,Peng, Lei,Li, Shan,Zhang, Nan,Liu, Yidong,Yan, Hailong
supporting information, p. 4959 - 4963 (2018/08/24)
A simultaneous asymmetric Mannich reaction and the construction of axially chiral sulfone-containing styrenes in one pot from α-amido sulfones based on the waste-reuse strategy was demonstrated. A series of chiral β-amino diesters and axially chiral sulfone-containing styrenes with various functional groups were synthesized in good to excellent yields and enantioselectivities under mild conditions. In addition, this protocol has been successfully applied to synthesize the anti-HIV drug Maraviroc and chiral trichloro derivatives.
METHOD FOR SYNTHESIZING β-AMINO-DITHIOESTER COMPOUND AND β-AMINO-DITHIOESTER COMPOUND SYNTHESIZED BY THE METHOD
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Paragraph 0501; 0502; 0506; 0535, (2017/12/01)
Disclosed is a production method of an N-protected-beta-amino-dithioester compound. To produce the N-protected-andbeta;-amino-dithioester compound, dithiomalonate may asymmetrically react with N-protected-imine or N-protected-alpha-amidosulfone according to the Mannich reaction in the presence of a chiral catalyst comprising a quaternary amide functional group and a quinuclidine functional group. According to the production method, chiral N-protected-beta-amino-dithioester can be synthesized with high optical selectivity at a high yield using a catalyst which is remarkably inexpensive and safe as compared with conventional metal catalysts.COPYRIGHT KIPO 2017
Enantioselective Additions of Stabilized Carbanions to Imines Generated from α-Amido Sulfones by Using Lipophilic Salts of Chiral Tris(1,2-diphenylethylenediamine) Cobalt(III) Trications as Hydrogen Bond Donor Catalysts
Joshi, Hemant,Ghosh, Subrata K.,Gladysz, John A.
, p. 3905 - 3915 (2017/08/29)
The enantiopure salt -[Co((S, S)-dpen) 3 ] 3+ 2Cl - BAr f - [BAr f = B(3,5-C 6 H 3 (CF 3) 2) 4 ] is an effective hydrogen bond donor catalyst (10 mol%, r.t., CH 2 Cl 2) for enantioselective additions of dialkyl malonates to Boc-derivatized aryl imines generated from sulfones [ArCH(SO 2 Ph)NHBoc] in the presence of K 2 CO 3 (ten examples, 91-97% isolated yields, 87-99% ee). The diastereomeric salt Λ-[Co((S, S)-dpen) 3 ] 3+ 2Cl - BAr f20 - [BAr f20 - = B(C 6 F 5) 4 - ] is similarly applied to additions of nitroalkanes (four examples, 89-93% isolated yields, 79-91% ee). Precautions to exclude air or moisture are unnecessary.
Asymmetric dual-reagent catalysis: Mannich-type reactions catalyzed by ion pair
Wang, Hong-Yu,Zhang, Kai,Zheng, Chang-Wu,Chai, Zhuo,Cao, Dong-Dong,Zhang, Jia-Xing,Zhao, Gang
supporting information, p. 1775 - 1779 (2015/02/19)
The combination of a new bifunctional phosphine and an acrylate generate a zwitterion in situ and it serves as an efficient catalyst for asymmetric reactions through a homogeneous ion-pairing mode. This new catalytic system has been successfully applied t
Asymmetric mannich reaction of malonates with aldimines using YbIII-pybox complexes supported on self-assembled organic-inorganic hybrid silica with an imidazolium framework
Karimi, Babak,Jafari, Ehsan,Enders, Dieter
, p. 7253 - 7258 (2015/02/02)
Yb(OTf)3/iPr-pybox (3b) immobilized on a self-assembled organic-inorganic hybrid silica with ionic liquid phase (SAILP) (Catalyst A) behaves as an efficient and recyclable catalyst in the enantioselective Mannich reaction of malonate esters wit
Highly efficient catalytic enantioselective mannich reaction of malonates with N-tert-butoxycarbonyl imines by using Yb(OTf)3/pybox catalysts at room temperature
Karimi, Babak,Jafari, Ehsan,Enders, Dieter
, p. 10142 - 10145 (2013/09/02)
Go Mannich! A highly efficient and enantioselective method for the direct asymmetric reaction of dibenzyl malonate with N-tert-butoxycarbonyl aldimines in the presence of Yb(OTf)3 and iPr-pybox complexes is described (see scheme; pybox=pyridine
Asymmetric Mannich reaction of malonates with imines catalyzed by a chiral calcium complex
Poisson, Thomas,Tsubogo, Tetsu,Yamashita, Yasuhiro,Kobayashi, Shu
supporting information; experimental part, p. 963 - 965 (2010/05/19)
(Chemical Equation Presented) Achiral calcium complex was found to be effective for the Mannich reactions of malonates with N-Boc imines. The desired adducts were obtained in excellent yields (up to 95%) with moderate to good enantioselectivities (up to 77% ee).
Solvent-dependent enantiodivergent mannich-type reaction: Utilizing a conformationally flexible guanidine/bisthiourea organocatalyst
Sohtome, Yoshihiro,Tanaka, Shinji,Takada, Keisuke,Yamaguchi, Takahisa,Nagasawa, Kazuo
supporting information; experimental part, p. 9254 - 9257 (2011/02/22)
Flex control: Malonate and tert-butoxycarbonyl (Boc)-protected imines react in the presence of the flexible catalyst 1 to furnish the S or the R adduct depending upon the solvent used. Kinetic analyses in this enantiodivergent organocatalysis show that en
Asymmetric Mannich-type reaction of aromatic α-amido sulfone with malonate using guanidine-thiourea bifunctional organocatalyst
Takada, Keisuke,Tanaka, Shinji,Nagasawa, Kazuo
experimental part, p. 1643 - 1646 (2009/12/03)
Asymmetric Mannich-type reaction of aromatic α-amido sulfone with malonate, catalyzed by a guanidine-thiourea bifunctional organocatalyst, affords β-amino acid derivatives in high yield with good to excellent enantioselectivity. Georg Thieme Verlag Stuttg
