80816-30-4Relevant academic research and scientific papers
Enantioselective Iridium-Catalyzed α-Allylation with Aqueous Solutions of Acetaldehyde
Carreira, Erick M.,Sandmeier, Tobias
supporting information, (2020/02/15)
The enantioselective α-allylation of aqueous solutions of acetaldehyde using iridium- A nd amine-catalyzed substitution of racemic allylic alcohols is described. The method utilizes a readily available, safely handled aqueous solution of acetaldehyde and furnishes ?,?-unsaturated aldehydes in good yields and greater than 99% enantiomeric excess. The synthetic potential of the method is demonstrated with the enantioselective formal syntheses of heliannuols C and E as well as heliespirones A and C.
Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System
Fujita, Shoji,Abe, Masanori,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 3822 - 3825 (2015/08/18)
A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.
Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes
Zhang, Guozhu,Cui, Li,Wang, Yanzhao,Zhang, Liming
supporting information; experimental part, p. 1474 - 1475 (2010/04/04)
(Chemical Equation Presented) Homogeneous carboamination, carboalkoxylation and carbolactonization of terminal alkenes are realized via oxidative gold catalysis, providing expedient access to various substituted Nor O-heterocycles. Deuterium-labeling studies established the anti nature of the alkene functionalization and the indispensible role of Au(I)/Au(III) catalysis. This study constitutes the first example of catalytically converting C(sp 3)-Au bonds into C(sp3)-C(sp2) bonds in a crosscoupling manner and opens new opportunities to study gold alkene catalysis where alkylgold intermediates can be readily functionalized intermolecularly. Copyright
Highly regio- and stereoselective addition of organolithium reagents to extended conjugate amides using (S,S)-(+)-pseudoephedrine as chiral auxiliary
Ocejo, Marta,Carrillo, Luisa,Badia, Dolores,Vicario, Jose L.,Fernandez, Naiara,Reyes, Efraim
supporting information; experimental part, p. 4404 - 4407 (2009/09/06)
(Chemical Equation Presented) The conjugate addition of organolithium reagents to polyunsaturated conjugate amides containing (S,S)-(+)- pseudoephedrine as chiral auxiliary has been studied in detail. The reaction proceeded with good 1,4-selectivity and e
Multicatalytic synthesis of complex tetrahydrofurans involving bismuth(iii) triflate catalyzed intramolecular hydroalkoxylation of unactivated olefins
Kelly, Brendan D.,Allen, Julia M.,Tundel, Rachel E.,Lambert, Tristan H.
supporting information; experimental part, p. 1381 - 1383 (2009/10/02)
A multicatalytic synthesis of complex tetrahydrofurans has been developed involving a Bi(OTf)3-catalyzed nucleophilic addition/ hydroalkoxylation sequence. Complex tetrahydrofuranyl products may be formed rapidly in high yield and with good diastereoselectivity. The demonstrated scope of hydroalkoxylation has also been expanded to include substrates bearing useful functional handles including carboxylate ester, olefin, nitrile, and nitro groups.
Copper-catalysed intramolecular O-H addition to unactivated alkenes
Adrio, Luis A.,Quek, Louisa Shuyi,Taylor, Jason G.,Kuok (Mimi) Hii, King
supporting information; experimental part, p. 10334 - 10338 (2010/02/28)
Intramolecular cyclisation of ω-alkenoic acids and alkenols can be achieved using a catalytic amount of Cu(OTf)2 to afford lactones and cyclic ethers, offering a practical alternative to existing catalysts.
A ring-closing metathesis approach to cyclic α,β-dehydroamino acids
Hekking, Koen F. W.,Waalboer, Dennis C. J.,Moelands, Marcel A. H.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
supporting information; scheme or table, p. 95 - 106 (2009/04/10)
A comprehensive study on the synthesis and ring-closing metathesis (RCM) of α,β-dehydroamino acids is described. This sequence has led to the formation of a range of biologically relevant functionalized nitrogen heterocycles. The incorporation of chiral b
Synthesis of 4,4′-disubstituted azepines via ring-closing metathesis reaction and asymmetric arylation of lactones
Delhaye, Laurent,Merschaert, Alain,Diker, Khalid,Houpis, Ioannis N.
, p. 1437 - 1442 (2007/10/03)
The syntheses of the title compounds were accomplished via an original sequence of reactions including the ring-closing metathesis of ω-dienes by using the second-generation Grubbs' catalyst. The chiral diene precursors are available in racemic or optical
Stereoselective cyclization using palladium(II) catalyst via hemiacetal intermediates
Miyazawa, Masahiro,Hirose, Yukari,Narantsetseg, Magsarjav,Yokoyama, Hajime,Yamaguchi, Seiji,Hirai, Yoshiro
, p. 2883 - 2886 (2007/10/03)
A stereoselective palladium-catalyzed cyclization of 3-phenyl-7-hydroxy-5- heptenal was developed. The reaction was carried out to give 2,4,6-trisubstituted tetrahydropyran with highly controlled 4,6-cis stereochemistry.
Copper(I) catalysts for the stereoselective addition of N-chloroamines to double bonds: A diastereoselective radical cyclisation
Heuger, Gerold,Kalsow, Stefanie,Gottlich, Richard
, p. 1848 - 1854 (2007/10/03)
Copper(I) catalysts for the diastereoselective radical cyclisation of N-chloro-N-pentenylamines have been developed. The stereoselectivity of the cyclisation depends upon the ligands employed, proving that the radical is bound to the catalyst during the formation of the new stereocentre and making a catalyst-influenced stereoselective radical reaction possible. The influence of the catalyst on the Beckwith-Houk transition states is discussed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
