Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

2018 ◽  
Vol 42 (3) ◽  
pp. 1608-1611 ◽  
Author(s):  
Yuxin Liu ◽  
Jingdong Wang ◽  
Zhonglin Wei ◽  
Jungang Cao ◽  
Dapeng Liang ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Phase Transfer ◽  
Cinchona Alkaloid ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Chiral Phase Transfer Catalysts

A series of 3-substituted 3-amino-oxindoles were constructed in excellent yields (96–99%) with high enantioselectivities (up to 95% ee) and diastereoselectivities (up to 95 : 5 dr) catalyzed by Cinchona alkaloid-derived phase-transfer catalysts.

Asymmetric synthesis of β-amino ketones by using cinchona alkaloid-based chiral phase transfer catalysts

2018 ◽  
Vol 16 (45) ◽  
pp. 8704-8709 ◽  
Author(s):  
Weihua Li ◽  
Yifeng Wang ◽  
Danqian Xu
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Phase Transfer ◽  
Cinchona Alkaloid ◽  
Reaction Products ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Chiral Phase Transfer Catalysts ◽  
The Mannich Reaction ◽  
High Yields

A highly enantioselective nucleophilic addition of ketones to versatile imines catalyzed by chiral PTC has been developed, and the process affords the Mannich reaction products with tertiary stereocenters in good to high yields and excellent enantioselectivities. This protocol is effective for gram scale reaction.

9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

2014 ◽  
Vol 12 (41) ◽  
pp. 8336-8345 ◽  
Author(s):  
Wenwen Peng ◽  
Jingwei Wan ◽  
Bing Xie ◽  
Xuebing Ma
Keyword(s):  
Schiff Base ◽  
Phase Transfer ◽  
Cinchona Alkaloid ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Chiral Phase Transfer Catalysts ◽  
High Yields

9-Amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts achieved high yields (92–99%) and excellent enantioselectivities (87–96% ee) in the enantioselective α-alkylation of glycine Schiff base.

scholarly journals Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2774 ◽  
Author(s):  
Yumeng Liang ◽  
Mayaka Maeno ◽  
Zhengyu Zhao ◽  
Norio Shibata
Keyword(s):  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Cinchona Alkaloid ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Excellent Yield ◽  
Chiral Phase Transfer Catalysts ◽  
Moderate Yield

The organo-catalyzed enantioselective benzylation reaction of α-trifluoromethoxy indanones afforded α-benzyl-α-trifluoromethoxy indanones with a tetrasubstituted stereogenic carbon center in excellent yield with moderate enantioselectivity (up to 57% ee). Cinchona alkaloid-based chiral phase transfer catalysts were found to be effective for this transformation, and both enantiomers of α-benzyl-α-trifluoromethoxy indanones were accessed, depended on the use of cinchonidine and cinchonine-derived catalyst. The method was extended to the enantioselective allylation reaction of α-trifluoromethoxy indanones to give the allylation products in moderate yield with good enantioselectivity (up to 76% ee).

Organic base-promoted enantioselective electrophilic cyanation of β-keto esters by using chiral phase-transfer catalysts

2015 ◽  
Vol 13 (33) ◽  
pp. 8812-8816 ◽  
Author(s):  
Min Chen ◽  
Zhi-Tang Huang ◽  
Qi-Yu Zheng
Keyword(s):  
Phase Transfer ◽  
Cinchona Alkaloid ◽  
Hypervalent Iodine ◽  
Organic Base ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Keto Esters ◽  
Chiral Phase Transfer Catalysts

Highly enantioselective electrophilic cyanation of β-keto esters with hypervalent iodine(iii) as the cyanating reagent induced by cinchona alkaloid-based chiral phase-transfer catalysts using an organic base is reported.

scholarly journals Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis

2019 ◽  
Author(s):  
Yumeng Liang ◽  
Mayaka Maeno ◽  
Zhengyu Zhao ◽  
Norio Shibata
Keyword(s):  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Cinchona Alkaloid ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Excellent Yield ◽  
Chiral Phase Transfer Catalysts ◽  
Moderate Yield

The organo-catalyzed enantioselective benzylation reaction of α-trifluoromethoxy indanones afforded α-benzyl-α-trifluoromethoxy indanones with a tetrasubstituted stereogenic carbon center in excellent yield with moderate enantioselectivity (up to 57% ee). Cinchona alkaloid-based chiral phase transfer catalysts were found to be effective for this transformation, and both enantiomers of α-benzyl-α-trifluoromethoxy indanones were accessed, depended on the use of cinchonidine and cinchonine-derived catalyst. The method was extended to the enantioselective allylation reaction of α-trifluoromethoxy indanones to give the allylation products in moderate yield with good enantioselectivity (up to 76% ee).

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