Enantioselective Synthesis of CF3 -Containing 3,2’-Pyrrolidinyl Spirooxindoles and Dispirooxindoles via Thiourea-Catalyzed Domino Michael/Mannich [3+2] Cycloaddition Reactions

2019 ◽  
Vol 361 (5) ◽  
pp. 1064-1070 ◽  
Author(s):  
Ye Lin ◽  
Yong-Xing Song ◽  
Da-Ming Du
Keyword(s):  
Enantioselective Synthesis ◽  
Cycloaddition Reactions

scholarly journals Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Long Li ◽  
Shan Wang ◽  
Pengfei Luo ◽  
Ran Wang ◽  
Zheng Wang ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Enantioselective Synthesis ◽  
Direct Access ◽  
Cycloaddition Reactions ◽  
Drug Discovery And Development ◽  
Spirocyclic Compounds ◽  
And Control ◽  
By Products

AbstractSpirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon−hydrogen (C−H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.

Enantioselective Synthesis of β-Trifluoromethyl-β-lactones via NHC-Catalyzed Ketene−Ketone Cycloaddition Reactions

2009 ◽  
Vol 11 (18) ◽  
pp. 4029-4031 ◽  
Author(s):  
Xiao-Na Wang ◽  
Pan-Lin Shao ◽  
Hui Lv ◽  
Song Ye
Keyword(s):  
Enantioselective Synthesis ◽  
Cycloaddition Reactions

scholarly journals Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones

2015 ◽  
Vol 6 (12) ◽  
pp. 7319-7325 ◽  
Author(s):  
De Wang ◽  
Guo-Peng Wang ◽  
Yao-Liang Sun ◽  
Shou-Fei Zhu ◽  
Yin Wei ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Cycloaddition Reactions ◽  
Catalytic Asymmetric

The first regioselective catalytic asymmetric [3 + 2] cycloaddition of benzofuranone-derived olefins with allenoates and substituted allenoates has been developed in the presence of (R)-SITCP.

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