ChemInform Abstract: ORGANOIRON COMPLEXES IN ORGANIC SYNTHESIS. PART 3. AN APPROACH TO THE SYNTHESIS OF SPIROCYCLIC COMPOUNDS FROM TRICARBONYLDIENEIRON COMPLEX INTERMEDIATES

1979 ◽  
Vol 10 (33) ◽  
Author(s):  
A. J. PEARSON
Keyword(s):  
Organic Synthesis ◽  
Spirocyclic Compounds ◽  
Organoiron Complexes

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.

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