Cleavage of carbon-carbon bonds with high stereochemical control. 7. Chiral .alpha.-silyl benzoylcycloalkanes undergo base-catalyzed cleavage with retention of configuration when not sterically congested

1989 ◽  
Vol 54 (6) ◽  
pp. 1408-1418 ◽  
Author(s):  
Leo A. Paquette ◽  
George D. Maynard ◽  
Choon Sup Ra ◽  
Manfred Hoppe
Keyword(s):  
Stereochemical Control ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

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.

scholarly journals Broad scope gold(i)-catalysed polyenyne cyclisations for the formation of up to four carbon–carbon bonds

2017 ◽  
Vol 15 (10) ◽  
pp. 2163-2167 ◽  
Author(s):  
Zhouting Rong ◽  
Antonio M. Echavarren
Keyword(s):  
Single Step ◽  
Simultaneous Formation ◽  
Broad Scope ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
First Time ◽  
High Stereoselectivity

The polycyclisation of polyeneynes catalyzed by gold(i) has been extended for the first time to the simultaneous formation of up to four carbon–carbon bonds, leading to steroid-like molecules with high stereoselectivity in a single step with low catalyst loadings.

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