Palladium- and platinum-catalysed addition of aldehydes with allylstannanes

The reaction of allylic stannanes 1 with aldehydes 2(or a ketone) takes place in the presence of catalytic amounts of PdCl2(PPh3)2 or PtCl2(PPh3)2 to give the corresponding homoallyl alcohols 3 in good to high yields.

[1]  Yoshinori Yamamoto,et al.  SELECTIVE REACTIONS USING ALLYLIC METALS , 1993 .

[2]  Y. Naruta,et al.  Versatile roles of Lewis acids in the reactions of allylic tin compounds , 1993 .

[3]  N. Isaacs,et al.  The stereochemistry of high pressure aldehyde addition to allylstannanes , 1992 .

[4]  Y. Masuyama,et al.  Palladium-catalyzed carbonyl allylation by allylic alcohols with stannous chloride , 1992 .

[5]  E. J. Thomas,et al.  1,5-Asymmetric induction in reactions betweenδ-alkoxyallylstannanes and aldehydes induced by tin (IV) chloride , 1990 .

[6]  B. Trost,et al.  Palladium-catalyzed trimethylenemethane reaction to form methylenetetrahydrofurans: reactions of substituted TMM precursors and mechanistic interpretation , 1990 .

[7]  S. Castellino,et al.  The mechanism of tin tetrachloride promoted additions of allylstannanes to aldehydes: a response to Denmark, Wilson, and Willson , 1989 .

[8]  E. J. Thomas,et al.  On the stereoselectivity of reaction between α-methylbut-2-enylstannanes and aldehydes , 1989 .

[9]  Y. Masuyama,et al.  Allylic alcohols as synthons of allylic carbanions. Palladium-catalyzed carbonyl allylation by allylic alcohols with tin dichloride , 1988 .

[10]  A. Boaretto,et al.  Allylstannation: IX. The preparation of 4-chloro-2,6-dialkyl-, 4-bromo-2,6-dialkyl-, (E/Z)-4-chloro-2,6-dialkyl-3-methyl-and (E/Z)-4-bromo-2,6-dialkyl-3-methyl-tetrahydropyrans by condensation of aldehydes with di- and tri-halides of allyltin☆ , 1986 .

[11]  K. Maruyama,et al.  Stereo- and regiocontrol of acyclic systems via the lewis acid mediated reaction of allylic stannanes with aldehydes , 1984 .

[12]  J. Labadie,et al.  Synthetic utility of the palladium-catalyzed coupling reaction of acid chlorides with organotins , 1983 .

[13]  Y. Naruta,et al.  Erythro-selective addition of crotyltrialkyltins to aldehydes regardless of the geometry of the crotyl unit. Stereoselection independent of the stereochemistry of precursors , 1980 .

[14]  P. W. Jolly,et al.  Transition metal allyls ☆: III. The (η3-allyl)2M complexes of nickel, palladium and platinum: structural considerations , 1980 .

[15]  R. Goddard,et al.  Transition metal allyls ☆: IV. The (η3-allyl)2M complexes of nickel, palladium and platinum: reaction with tertiary phosphines , 1980 .

[16]  H. Kurosawa,et al.  .pi.-Allylmetal chemistry. 6. Synthesis and equilibriums of unusually stable .sigma.-allylplatinum(II) and -palladium(II) complexes containing polyhaloaryl groups , 1977 .