Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 36, Pages 16298-16302Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c07394
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Funding
- Israel Academy of Sciences and Humanities [487/21]
- European Union [101028628]
- European Research Council under the Excellence Science H2020 Program of the European Community [786976]
- Marie Curie Actions (MSCA) [101028628] Funding Source: Marie Curie Actions (MSCA)
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Here, we demonstrate a method to form acyclic frameworks with two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This approach involves regio-and diastereoselective hydro or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes by adding nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivers the desired compounds.
Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio-and diastereoselective hydro or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes of the latter via the addition of nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivered the title compounds.
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