115352-39-1Relevant academic research and scientific papers
Synthesis of 2,5-disubstituted dihydrofuran-3(2 H)-ones via [2,3]-sigmatropic rearrangement of oxonium ylides generated from α-oxo gold carbenes
Han, Miyeon,Bae, Joohee,Choi, Juhee,Tae, Jinsung
supporting information, p. 2077 - 2080 (2013/10/21)
Novel [2,3]-sigmatropic rearrangements of oxonium ylides generated from α-oxo gold carbenes were discovered. An efficient synthetic method of 2,5-disubstituted dihydrofuran-3(2H)-ones via gold-catalyzed intermolecular oxidation of the allyl homopropargyl ethers with N-oxide was developed. And the synthetic utility of the current method has been proved by concise formal synthesis of (±)-kumausallene. Georg Thieme Verlag Stuttgart, New York.
Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols
Li, Zhanjie,Parr, Brendan T.,Davies, Huw M. L.
supporting information; experimental part, p. 10942 - 10946 (2012/08/07)
The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium carbenoids and chiral allyl alcohols is a convergent C-C bond forming process, which generates two vicinal stereogenic centers. Any of the four possible stereoisomers can be selectively synthesized by appropriate combination of the chiral catalyst Rh2(DOSP)4 and the chiral alcohol.
Synthesis and absolute configuration of the 7-phenylhepta-4,6-diyne-1,2- diol isolated from Bidens pilosa
Cui, Shan,Zou, Yang,Wu, Yikang,Gao, Po
, p. 2131 - 2135 (2011/08/04)
The title diynediol was synthesized in enantiopure (>98.4% ee) forms, with the cross coupling of phenylacetylene with either (R)- or (S)-5-benzyloxypent-1-yn-4-ol catalyzed by nickel(II) chloride-copper(I) iodide as the key step. Comparison of the spectro
Zinc-catalyzed allenylations of aldehydes and ketones
Fandrick, Daniel R.,Saha, Jaideep,Fandrick, Keith R.,Sanyal, Sanjit,Ogikubo, Junichi,Lee, Heewon,Roschangar, Frank,Song, Jinhua J.,Senanayake, Chris H.
supporting information; experimental part, p. 5616 - 5619 (2011/12/03)
The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective B/Zn exchange to generate a propargyl zinc int
First stereoselective synthesis of synargentolide A and revision of absolute stereochemistry
Sabitha, Gowravaram,Gopal, Peddabuddi,Reddy, C. Nagendra,Yadav
scheme or table, p. 6298 - 6302 (2010/01/18)
The first stereoselective total synthesis of synargentolide A isolated from Syncolostemon argenteus has been achieved from commercially available (R)-benzyl glycidyl ether using Sharpless asymmetric epoxidation and cross-metathesis reactions as the key st
Chemical variation of natural product-like scaffolds: Design and synthesis of spiroketal derivatives
Zinzalla, Giovanna,Milroy, Lech-Gustav,Ley, Steven V.
, p. 1977 - 2002 (2008/02/04)
The design and synthesis of spiroketal structures and their chemical modification, leading to a collection of new small molecules for biological evaluation as orally-bioavailable lead compounds is described. Both [6,5]- and [6,6]-membered ring spiroketal units have been prepared in a stereochemically-varying fashion starting from commercially available (R)- or (S)-glycidol, in ten, eleven and twelve linear steps, in overall yields of 45, 40 and 20%, respectively. Further elaboration according to Lipinski's guidelines has given a collection of structurally-diverse, new spiroketal derivatives in high yields and with high purity. The Royal Society of Chemistry 2006.
Double conjugate addition of dithiols to propargylic carbonyl systems to generate protected 1,3-dicarbonyl compounds
Sneddon, Helen F.,Van Den Heuvel, Alexandra,Hirsch, Anna K. H.,Booth, Richard A.,Shaw, David M.,Gaunt, Matthew J.,Ley, Steven V.
, p. 2715 - 2725 (2007/10/03)
The work describes the efficient double conjugate addition of ethane and propane dithiols in the presence of sodium methoxide to a wide variety of propargylic carbonyl containing compounds. The products of these reactions are differentiated, 1,3-dicarbony
Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: Efficient and general trans addition
Trost, Barry M.,Ball, Zachary T.
, p. 17644 - 17655 (2007/10/03)
The complex [Cp*Ru(MeCN)3]PF6 is shown to catalyze the hydrosilylation of a wide range of alkynes, Terminal alkynes afford access to α-vinylsilane products with good regioselectivity. Deuterium labeling studies indicate a clean trans
Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality.
Trost, Barry M,Machacek, Michelle R,Ball, Zachary T
, p. 1895 - 1898 (2007/10/03)
[reaction: see text] Ruthenium-catalyzed alkyne hydrosilylation or silyl-alkyne Alder ene reactions provide entry into benzyldimethylsilyl (BDMS)-substituted alkenes. The BDMS-vinylsilanes are further elaborated through mild palladium-catalyzed cross coup
