A catalytic asymmetric synthesis of α-methylene lactones by the palladium-catalysed carbonylation of prochiral alkenyl halides

A catalytic asymmetric synthesis of the α-methylene lactones starting with the prochiral alkenyl halides 8 and 19 has been achieved for the first time, giving 9 in 57% enantiomeric excess (e.e.) and 20 in 39% e. e., respectively.

[1]  M. Shibasaki,et al.  Asymmetric Heck reaction: a catalytic asymmetric synthesis of the key intermediate for .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.-triol and .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.,14-tetrol , 1991 .

[2]  R. Grigg,et al.  Suppression of alkene isomerisation in products from intramolecular heck reactions by addition of Tl(1) salts. , 1991 .

[3]  K. Osakada,et al.  Mechanisms of double and single carbonylation reactions catalyzed by palladium complexes , 1991 .

[4]  Masahito,et al.  Synthesis of Ethynyl(phenyl)iodonium Tetrafluoroborate. : A New Reagent for Ethynylation of 1,3-Dicarbonyl Compounds. , 1991 .

[5]  M. Sodeoka,et al.  On the Role of Silver Salts in Asymmetric Heck-type Reaction. A Greatly Improved Catalytic Asymmetric Synthesis of cis-Decalin Derivatives , 1990 .

[6]  H. Alper,et al.  Asymmetric synthesis of acids by the palladium-catalyzed hydrocarboxylation of olefins in the presence of (R)-(-)- or (S)-(+)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate , 1990 .

[7]  M. Periasamy,et al.  A new, simple procedure for the generation and addition of HI to alkenes and alkynes using Bl3:N,N-diethylaniline complex and acetic acid , 1990 .

[8]  H. Alper,et al.  Poly-L-leucine as an added chiral ligand for the palladium catalysed carbonylation of allylic alcohols , 1990 .

[9]  M. Sodeoka,et al.  Catalytic asymmetric carbon-carbon bond formation: asymmetric synthesis of cis-decalin derivatives by palladium-catalyzed cyclization of prochiral alkenyl iodides , 1989 .

[10]  J. Bakos,et al.  Asymmetric hydroformylation with Pt-phosphine-SnCl2 and Pt-bisphosphine-CuCl2 (or CuCl) catalytic systems , 1989 .

[11]  A. Mortreux,et al.  Utilisation des ligands aminophosphinephosphinites en hydroformylation catalysée par le rhodium: amélioration de l'énantioselectivité par synthèse selective des hydrures RhH(CO)2L★2 , 1989 .

[12]  W. R. Jackson,et al.  Hydroformylation of tricarbonyl(η6-styrene)chromium and related compounds , 1989 .

[13]  M. Choukrad,et al.  Asymmetric carbonylation of .alpha.-methylbenzyl bromide catalyzed by oxazaphospholane-palladium complexes under phase-transfer conditions , 1988 .

[14]  G. Parrinello,et al.  Asymmetric hydroformylation catalyzed by homogeneous and polymer-supported platinum complexes containing chiral phosphine ligands , 1987 .

[15]  L. Kollár,et al.  Asymmetric hydroformylation of unsaturated esters with PtCl(SnCl3)[(R,R)-DIOP] catalyst , 1987 .

[16]  Takakazu Yamamoto,et al.  Mechanisms of double and single carbonylation reactions of aryl iodides catalyzed by palladium complexes to give .alpha.-keto esters and esters , 1987 .

[17]  H. Mazdiyasni,et al.  Asymmetric microbial reduction of prochiral 2,2,-disubstituted cycloalkanediones , 1987 .

[18]  G. Consiglio,et al.  Asymmetric hydroformylation of the linear butenes by [(R,R)-Diop]Pt(SnCl3)Cl , 1985 .

[19]  G. Chiusoli,et al.  Asymmetric induction in carbonmethoxylation of vinylaromatics , 1982 .

[20]  Toshi-aki Kobayashi,et al.  Palladium complex-catalyzed carbonylation of organic halides in the presence of cyclic ethers: Halohydrin ester synthesis , 1982 .

[21]  G. Consiglio.  Asymmetric hydrocarboxylation of olefins , 1977 .

[22]  S. M. Kupchan,et al.  Tumor inhibitors. 69. Structure-cytotoxicity relationships among the sesquiterpene lactones. , 1971, Journal of medicinal chemistry.