Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.
Liu, Jianzhong,Wen, Xiaojin,Qin, Chong,Li, Xinyao,Luo, Xiao,Sun, Ao,Zhu, Bencong,Song, Song,Jiao, Ning
supporting information
p. 11940 - 11944
(2017/09/20)
New tandem radical cyclizations directed toward the synthesis of crinipellin A
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Schwartz,Curran
p. 9272 - 9284
(2007/10/02)
Regiochemistry of Nucleophilic Opening of β-Substituted Styrene Oxides with Thiolate Anions: Model Experiments in the Synthesis of Leukotriene Analogues
β-Substituted trans-styrene oxides are cleaved with thiolate anions highly regioselectively by attack at the α-carbon whereas the cis-isomers are cleaved by attack at the α- and β-carbons.Cysteine, in a suitably protected form, similarly cleaves β-substituted trans-styrene oxides, thus allowing the synthesis of a simple LTE model.
Marples, Brian A.,Saint, Christopher G.,Traynor, John R.
p. 567 - 574
(2007/10/02)
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