57642-64-5Relevant academic research and scientific papers
Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives
Du, Xiang-Wei,Stanley, Levi M.
, p. 3276 - 3279 (2015)
Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes and substituted salicylaldehyes. The resulting 2,3-disubstituted chroman-4-ones are readily fluorinated to form trans-3-fluoro-2,3-disubstituted chroman-4-ones in high yields with excellent diastereoselectivity. (Chemical Equation Presented).
TMSOTf-promoted addition of alkynes to aldehydes: A novel synthesis of chroman-4-ones
Ji, Yeon Park,Ullapu, Punna Reddy,Choo, Hyunah,Jae, Kyun Lee,Min, Sun-Joon,Ae, Nim Pae,Kim, Youseung,Baek, Du-Jong,Yong, Seo Cho
experimental part, p. 5461 - 5469 (2009/05/07)
A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Reaction of 2-hydroxybenzaldehydes with alkynes, alkenes, or allenes via cleavage of the aldehyde C-H bond using a rhodium catalyst system
Kokubo, Ken,Matsumasa, Kenji,Nishinaka, Yuko,Miura, Masahiro,Nomura, Masakatsu
, p. 303 - 311 (2007/10/03)
2-Hydroxybenzaldehydes smoothly and efficiently react with various internal and terminal alkynes accompanied by cleavage of the aldehyde C-H bond by using a rhodium-based catalyst system of [RhCl(cod)]2/dppf/Na2CO3 [cod = 1,5-cyclooctadiene; dppf = 1,1'-bis(diphenylphosphino)ferrocene] to give the corresponding 2-alkenoylphenols in good to excellent yields. The regioselectivity of the reaction depends on the substituents of acetylene; an oxygen function on the propargylic position shows a considerable directing effect. The aldehydes can also react with some alkenes or allenes, such as triethylvinylsilane and 2-norbornene or 3-methyl-1,2-butadiene and 1,2- nonadienes, in place of alkynes.
