83188-25-4Relevant academic research and scientific papers
Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades
May, Jeremy A.,Wang, Qinxuan
, p. 3039 - 3044 (2020/04/20)
A nitrene/alkyne cascade reaction terminating in C-H bond insertion to form functionalized bridged azacycles from carbonazidates is presented. Due to an initial Huisgen cyclization, all carbonazidates reacted with the alkyne in an exo mode in contrast to the use of sulfamate esters, which react predominately in an endo mode. Substrates with different ring sizes as well as different aryl and heteroaryl groups were also explored. Variation of the nitrene tether showed that 7-membered rings were the maximum ring size to be formed by nitrene attack on the alkyne. Examples incorporating stereocenters on the carbonazidate's tether induced diasteroselectivity in the formation of the bridged ring and two new stereocenters. Additionally, propellanes containing aminals, hemiaminals, and thioaminals formed from the bridged azacycles in the same reaction via an acid-promoted rearrangement.
Rh(II)-Catalyzed Chemoselective Oxidative Amination and Cyclization Cascade of 1-(Arylethynyl)cycloalkyl)methyl Sulfamates
Pan, Dong,Wei, Yin,Shi, Min
supporting information, p. 3584 - 3587 (2017/07/15)
A Rh(II)-catalyzed chemoselective oxidative amination and cyclization cascade of 1-(arylethynyl)cycloalkyl)methyl sulfamates has been presented. For a cyclopropyl or cyclobutyl moiety containing alkynyl sulfamates, the reactions underwent a metallonitrene
Catalyst-dependent divergent synthesis of pyrroles from 3-alkynyl imine derivatives: A noncarbonylative and carbonylative approach
Chen, Gen-Qiang,Zhang, Xiao-Nan,Wei, Yin,Tang, Xiang-Ying,Shi, Min
supporting information, p. 8492 - 8497 (2014/08/18)
A novel Ru0- and RhI-catalyzed noncarbonylative and carbonylative cycloisomerization of readily available 3-alkynyl imine derivatives has been developed to provide 3,4-fused or nonfused pyrrole derivatives efficiently in moderate to
Gold-catalyzed hydrative carbocyclization of 1,5- and 1,7-allenynes mediated by π-allene complex: Mechanistic evidence supported by the chirality transfer of allenyne substrates
Yang, Chun-Yao,Lin, Guan-You,Liao, Hsin-Yi,Datta, Swarup,Liu, Rai-Shung
, p. 4907 - 4914 (2008/12/20)
(Chemical Equation Presented) We report PPh3AuCl/AgOTf-catalyzed hydrative carbocyclization of 1,5- and 1,7-allenynes to give cyclized ketones chemoselectively. In this transformation, hydration occurrs regioselectively at the C≡CPh carbon, acc
CHLOROACETYLENES AS MICHAEL ACCEPTORS. II. DIRECT ETHYNYLATION AND VINYLATION OF TERTIARY ENOLATES.
Kende, Andrew S.,Fludzinski, Pawel
, p. 2373 - 2376 (2007/10/02)
The reaction of ClCCCl, PhCCCl and PhSCCCl with a variety of tertiary enolates leads in 43-90percent yields to α-chloroethynyl, α-phenylethynyl and α-thiophenylethynyl derivatives.The -CCCl group is smoothly converted to -CCH using copper p
