- Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones
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The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.
- Liu, Yonggui,Luo, Guoyong,Yang, Xing,Jiang, Shichun,Xue, Wei,Chi, Yonggui Robin,Jin, Zhichao
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supporting information
p. 442 - 448
(2019/11/25)
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- Tertiary amine compound, bisphosphine ligand, and intermediate and preparation method of tertiary amine compound
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The invention discloses a tertiary amine compound, a bisphosphine ligand, and an intermediate and a preparation method of the tertiary amine compound, and provides a tertiary amine compound preparation method, which comprises: under the protection of a ga
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Paragraph 0232; 0236; 0237
(2019/11/20)
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- Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to N-Unprotected Ketimines: Efficient Synthesis of Cipargamin
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Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO-BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin.
- Zhu, Jinbin,Huang, Linwei,Dong, Wei,Li, Naikai,Yu, Xingxin,Deng, Wei-Ping,Tang, Wenjun
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supporting information
p. 16119 - 16123
(2019/11/03)
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- Me-BIPAM for the synthesis of optically active 3-aryl-3-hydroxy-2-oxindoles by ruthenium-catalyzed addition of arylboronic acids to isatins
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A chiral O-linked C2-symmetric bidentate phosphoramidite (Me-BIPAM) was found to be efficient for the ruthenium-catalyzed addition of arylboronic acids to isatins. Asymmetric synthesis of 3-aryl-3-hydroxy-2- oxindoles by 1,2-addition of arylboronic acids to isatins was carried out in the presence of [RuCl2(PPh3)3]/(R,R)-Me-BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. It was found that the reaction with N-protected isatins proceeds with high yields and good enantioselectivities. The best protective groups on the nitrogen atom were different depending on the substituents on the aromatic ring. The use of a N-benzyl group resulted in excellent enantioselectivities in many substrates compared with other groups. Add it up: A chiral O-linked C2-symmetric bidentate phosphoramidite (Me-BIPAM) was found to be efficient for the ruthenium-catalyzed addition of arylboronic acids to isatins. Asymmetric synthesis of 3-aryl-3-hydroxy-2-oxindoles by 1,2-addition of arylboronic acids to isatins was carried out in the presence of [RuCl2(PPh 3)3]/(R,R)-Me-BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. Copyright
- Yamamoto, Yasunori,Miyaura, Norio,Yohda, Masaaki,Shirai, Tomohiko,Ito, Hajime
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supporting information
p. 2446 - 2449,4
(2020/08/24)
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- Construction of chiral quaternary carbon through morita-baylis-hillman reaction: An enantioselective approach to 3-substituted 3-hydroxyoxindole derivatives
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A new enantioselective approach to obtain a tetrasubstituted chiral center at the C3 position of oxindoles via a catalytic asymmetric Morita-Baylis-Hillman reaction has been demonstrated. This reaction provides 3-substituted 3-hydroxy-2-oxindoles in good
- Guan, Xiao-Yang,Wei, Yin,Shi, Min
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supporting information; experimental part
p. 13617 - 13621
(2011/03/18)
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