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Synthesis 2016; 48(19): 3279-3286
DOI: 10.1055/s-0035-1561666
DOI: 10.1055/s-0035-1561666
paper
Formation of Carbon Quaternary Stereogenic Center in Acyclic Systems via a Sequence of Carbometalation–Intramolecular Cyclization–Silicon Activation
Further Information
Publication History
Received: 13 April 2016
Accepted after revision: 20 May 2016
Publication Date:
10 June 2016 (online)
Dedicated to the memory of Jean Normant, a wonderful teacher and truly inspirational colleague
Abstract
The diastereoselective carbometalation reaction of cyclopropenyl esters followed by reaction with acylsilanes provides γ-silylated lactones that undergo a ‘sila-Grob’ fragmentation to give pyrone enolates as a new source of acyclic δ-diketones, δ-keto acid, and δ-keto ester derivatives possessing a quaternary stereocenter.
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For reviews published in 2014, see:
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For reviews, see:
For the enantioselective cyclopropenylation of alkynes, see:
For recent reviews on C–C cleavage, see: