Cleavage of carbon-carbon bonds with high stereochemical control. 6. Asymmetric synthesis of chiral C-centered organosilanes by Haller-Bauer cleavage of optically active, nonenolizable .alpha.-silyl phenyl ketones

1989 ◽  
Vol 54 (6) ◽  
pp. 1399-1408 ◽  
Author(s):  
John P. Gilday ◽  
Judith C. Gallucci ◽  
Leo A. Paquette
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Stereochemical Control ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Phenyl Ketones

scholarly journals Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles

Science ◽  
2020 ◽  
Vol 367 (6477) ◽  
pp. 559-564 ◽  
Author(s):  
Haohua Huo ◽  
Bradley J. Gorsline ◽  
Gregory C. Fu
Keyword(s):  
Nickel Catalyst ◽  
Organic Synthesis ◽  
Side Reactions ◽  
Substitution Reactions ◽  
Stereochemical Control ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Single Stereoisomer

Stereochemical control in the construction of carbon-carbon bonds between an alkyl electrophile and an alkyl nucleophile is a persistent challenge in organic synthesis. Classical substitution reactions via SN1 and SN2 pathways are limited in their ability to generate carbon-carbon bonds (inadequate scope, due to side reactions such as rearrangements and eliminations) and to control stereochemistry when beginning with readily available racemic starting materials (racemic products). Here, we report a chiral nickel catalyst that couples racemic electrophiles (propargylic halides) with racemic nucleophiles (β-zincated amides) to form carbon-carbon bonds in doubly stereoconvergent processes, affording a single stereoisomer of the product from two stereochemical mixtures of reactants.

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