The synthesis of spirocyclic compounds by regiospecific palladium catalysed cyclisation reactions
作者： Ronald Grigg , Visuvanathar Sridharan , Paul Stevenson , Sukanthini Sukirthalingam
DOI: 10.1016/S0040-4020(01)81034-6
关键词: Chemistry 、 Double bond 、 Isomerization 、 Yield (chemistry) 、 Palladium 、 Alkene 、 Tetraethylammonium chloride 、 Organic chemistry
摘要: Abstract Enamides derived from o-iodobenzoic acid and Z-3-bromoacrylic undergo regiospecific palladium catalysed exo-trig cyclisation onto a proximate alkene to give spirocyclic products in good excellent yield. Double bond isomerisation the product is not usually observed retarded by addition of tetraethylammonium chloride which also allows reaction be carried out under milder conditions.
elsevier.com
sci-hub.se 参考文章(19)
Kostas Karabelas, Christer Westerlund, Anders Hallberg, The effect of added silver nitrate on the palladium-catalyzed arylation of allyltrimethylsilanes Journal of Organic Chemistry. ,vol. 50, pp. 3896- 3900 ,(1985) , 10.1021/JO00220A042
Peter J. Harrington, Louis S. Hegedus, Keith F. McDaniel, Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. 2. Total synthesis of the N-acetyl methyl ester of (.+-.)-clavicipitic acids Journal of the American Chemical Society. ,vol. 109, pp. 4335- 4338 ,(1987) , 10.1021/JA00248A032
Kostas Karabelas, Anders Hallberg, Synthesis of (E)-(2-arylethenyl)silanes by palladium-catalyzed arylation of vinylsilanes in the presence of silver nitrate Journal of Organic Chemistry. ,vol. 51, pp. 5286- 5290 ,(1986) , 10.1021/JO00376A044
Ronald Grigg, Paul Stevenson, Tanachat Worakun, The regioselectivity of rhodium and palladium-catalysed cyclisations of 2-bromo-1,6- and -1,7-dienes Tetrahedron. ,vol. 44, pp. 2033- 2048 ,(1988) , 10.1016/S0040-4020(01)90346-1
Ronald Grigg, Paul Stevenson, Tanachat Worakun, Regiospecific formation of 1,3-dienes by the palladium catalysed intra- and inter-molecular coupling of vinyl halides.1 Tetrahedron. ,vol. 44, pp. 2049- 2054 ,(1988) , 10.1016/S0040-4020(01)90347-3
Miwako Mori, Nana Kanda, Izumi Oda, Yoshio Ban, New synthesis of heterocycles by use of palladium catalyzed cycli zation of α-haloamide with internal double bond Tetrahedron. ,vol. 41, pp. 5465- 5474 ,(1985) , 10.1016/S0040-4020(01)91346-8
Barry Burns, Ronald Grigg, Piniti Ratananukul, Visuvanathar Sridharan, Paul Stevenson, Tanachat Worakun, Palladium catalysed tandem cyclisation-anion capture processes.Hydride ion capture by alkyl- and π-allyl-palladium species Tetrahedron Letters. ,vol. 29, pp. 4329- 4332 ,(1988) , 10.1016/S0040-4039(00)80489-X
L. Shi, C. K. Narula, K. T. Mak, L. Kao, Y. Xu, R. F. Heck, Palladium-catalyzed cyclizations of bromodialkenyl ethers and amines Journal of Organic Chemistry. ,vol. 48, pp. 3894- 3900 ,(1983) , 10.1021/JO00170A005
Matthew M. Abelman, Taeboem Oh, Larry E. Overman, Intramolecular alkene arylations for rapid assembly of polycyclic systems containing quaternary centers. A new synthesis of spirooxindoles and other fused and bridged ring systems Journal of Organic Chemistry. ,vol. 52, pp. 4130- 4133 ,(1987) , 10.1021/JO00227A038
Tuyêt Jeffery, Highly stereospecific palladium-catalysed vinylation of vinylic halides under solid-liquid phase transfer conditions. Tetrahedron Letters. ,vol. 26, pp. 2667- 2670 ,(1985) , 10.1016/S0040-4039(00)98131-0