1010447-32-1Relevant articles and documents
A one-pot C-H insertion/olefination sequence for the formation of α-alkylidene-γ-butyrolactones
Lloyd, Matthew G.,Taylor, Richard J. K.,Unsworth, William P.
, p. 2772 - 2775 (2014)
A one-pot C-H insertion/olefination sequence for the conversion of α-diazo-α-(dialkoxyphosphoryl)acetates into α-alkylidene- γ-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate cataly
α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
Lloyd, Matthew G.,D'Acunto, Mariantonietta,Taylor, Richard J.K.,Unsworth, William P.
, p. 7107 - 7123 (2015/02/19)
Abstract A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.
Tin-free generation of alkyl radicals from alkyl 4-pentynyl sulfides via homolytic substitution at the sulfur atom
Bencivenni, Giorgio,Lanza, Tommaso,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Spagnolo, Piero,Zanardi, Giuseppe
supporting information; body text, p. 1127 - 1130 (2009/04/06)
Homolytic substitution at the sulfur atom of β-(phenylsulfanyl)vinyl radicals, obtained by radical reaction of benzenethiol with easily accessible alkyl 4-pentynyl sulfides, is a mild, effective, tin-free route for the generation of all types of alkyl radicals. This protocol can be employed in reductive defunctionalizations as well as cyclizations onto both electron-rich and electron-poor C-C double bonds.
