- The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: Enantioselective synthesis of β-amino acids
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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
- Song, Jun,Wang, Yi,Deng, Li
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- Asymmetric Mannich Reaction and Construction of Axially Chiral Sulfone-Containing Styrenes in One Pot from α-Amido Sulfones Based on the Waste-Reuse Strategy
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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.
- Li, Dongmei,Tan, Yu,Peng, Lei,Li, Shan,Zhang, Nan,Liu, Yidong,Yan, Hailong
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supporting information
p. 4959 - 4963
(2018/08/24)
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- METHOD FOR SYNTHESIZING β-AMINO-DITHIOESTER COMPOUND AND β-AMINO-DITHIOESTER COMPOUND SYNTHESIZED BY THE METHOD
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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
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Paragraph 0501; 0502; 0506; 0535
(2017/12/01)
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- 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
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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.
- Joshi, Hemant,Ghosh, Subrata K.,Gladysz, John A.
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p. 3905 - 3915
(2017/08/29)
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- Asymmetric dual-reagent catalysis: Mannich-type reactions catalyzed by ion pair
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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
- Wang, Hong-Yu,Zhang, Kai,Zheng, Chang-Wu,Chai, Zhuo,Cao, Dong-Dong,Zhang, Jia-Xing,Zhao, Gang
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supporting information
p. 1775 - 1779
(2015/02/19)
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- Asymmetric mannich reaction of malonates with aldimines using YbIII-pybox complexes supported on self-assembled organic-inorganic hybrid silica with an imidazolium framework
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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
- Karimi, Babak,Jafari, Ehsan,Enders, Dieter
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supporting information
p. 7253 - 7258
(2015/02/02)
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- Highly efficient catalytic enantioselective mannich reaction of malonates with N-tert-butoxycarbonyl imines by using Yb(OTf)3/pybox catalysts at room temperature
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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
- Karimi, Babak,Jafari, Ehsan,Enders, Dieter
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supporting information
p. 10142 - 10145
(2013/09/02)
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- Asymmetric Mannich reaction of malonates with imines catalyzed by a chiral calcium complex
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(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).
- Poisson, Thomas,Tsubogo, Tetsu,Yamashita, Yasuhiro,Kobayashi, Shu
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supporting information; experimental part
p. 963 - 965
(2010/05/19)
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- Solvent-dependent enantiodivergent mannich-type reaction: Utilizing a conformationally flexible guanidine/bisthiourea organocatalyst
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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
- Sohtome, Yoshihiro,Tanaka, Shinji,Takada, Keisuke,Yamaguchi, Takahisa,Nagasawa, Kazuo
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supporting information; experimental part
p. 9254 - 9257
(2011/02/22)
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- Asymmetric Mannich-type reaction of aromatic α-amido sulfone with malonate using guanidine-thiourea bifunctional organocatalyst
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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
- Takada, Keisuke,Tanaka, Shinji,Nagasawa, Kazuo
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experimental part
p. 1643 - 1646
(2009/12/03)
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- Organocatalytic asymmetric mannich reactions with JV-Boc and JV-Cbz protected α-amido sulfones (Boc: Tert-butoxycarbonyl, Cbz: Benzyloxycarbonyl)
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Different malonates and βketoesters can react with N-tert-butoxycarbonyl- (N-Boc) and N-benzyloxycarbonyl- (N-Cbz) protected α-amido sulfones in an organocatalytic asymmetric Mannich-type reaction. The reaction makes use of a simple and easily obtained ph
- Marianacci, Olindo,Micheletti, Gabriele,Bernardi, Luca,Fini, Francesco,Fochi, Mariafrancesca,Pettersen, Daniel,Sgarzani, Valentina,Ricci, Alfredo
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p. 8338 - 8351
(2008/04/01)
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