Rhodium-BisbenzodioxanPhos complex-catalyzed homogeneous enantioselective pauson-khand-type cyclization in alcoholic solvents

The chiral atropisomeric diphosphane ligand (S)-BisbenzodioxanPhos was found to be highly effective in the co-operative processeses of aldehyde decarbonylation and cascaded enantioselective Pauson-Khand-type reactions. Various 1,6-enynes were transformed to the corresponding bicyclic cyclopentenones in good yields and enantiomeric excesses (up to 96% ee). The attractive feature of this new Rh-catalyzed homogeneous dual catalysis system is that the reaction can be performed in alcoholic solution.

[1]  A. Chan,et al.  Rhodium-catalyzed asymmetric aqueous Pauson-Khand-type reaction. , 2005, Chemistry.

[2]  S. Gibson,et al.  The intermolecular Pauson-Khand reaction. , 2005, Angewandte Chemie.

[3]  J. Loch,et al.  A study of [Co2(alkyne)(binap)(CO)4] complexes (BINAP=(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine)). , 2005, Chemistry.

[4]  Andreas Lanver,et al.  A Pauson-Khand approach to new carbocyclic nucleoside analogs , 2005 .

[5]  J. Winkler,et al.  A Pauson-Khand approach to the synthesis of ingenol. , 2005, Organic letters.

[6]  G. Domínguez,et al.  The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules. , 2004, Chemical Society reviews.

[7]  K. Kakiuchi,et al.  Catalytic asymmetric Pauson–Khand-type reactions of enynes with formaldehyde in aqueous media , 2004 .

[8]  M. E. Krafft,et al.  When the Pauson-Khand and Pauson-Khand type reactions go awry: a plethora of unexpected results , 2004 .

[9]  K. Kakiuchi,et al.  Evolution of carbonylation catalysis: no need for carbon monoxide. , 2004, Angewandte Chemie.

[10]  J. Lex,et al.  Transition-metal-mediated synthesis of novel carbocyclic nucleoside analogues with antitumoral activity. , 2004, Chemistry.

[11]  G. Consiglio,et al.  Mechanistic and stereochemical aspects of the asymmetric cyclocarbonylation of 1,6-enynes with rhodium catalysts. , 2004, Chemical Communications.

[12]  A. Riera,et al.  PuPHOS: a synthetically useful chiral bidentate ligand for the intermolecular Pauson-Khand reaction. , 2004, The Journal of organic chemistry.

[13]  A. Greene,et al.  Asymmetric Pauson–Khand reaction with chiral, electron-deficient mono- and bis-phosphine ligands , 2004 .

[14]  B. Jiang,et al.  Highly enantioselective construction of fused pyrrolidine systems that contain a quaternary stereocenter: concise formal synthesis of (+)-conessine. , 2004, Angewandte Chemie.

[15]  Nakcheol Jeong,et al.  Desymmetrization of meso-dienyne by asymmetric Pauson-Khand type reaction catalysts. , 2004, Chemical communications.

[16]  V. Ratovelomanana-Vidal,et al.  Chiral biphenyl diphosphines for asymmetric catalysis: stereoelectronic design and industrial perspectives. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[17]  J. Genêt.  Asymmetric catalytic hydrogenation. Design of new Ru catalysts and chiral ligands: from laboratory to industrial applications. , 2003, Accounts of chemical research.

[18]  K. Brummond,et al.  Unique strategy for the assembly of the carbon skeleton of guanacastepene A using an allenic Pauson-Khand-type reaction. , 2003, Organic letters.

[19]  K. Kakiuchi,et al.  Aqueous catalytic Pauson-Khand-type reactions of enynes with formaldehyde: transfer carbonylation involving an aqueous decarbonylation and a micellar carbonylation. , 2003, Angewandte Chemie.

[20]  Susan E. Gibson,et al.  Pauson‐Khand‐Reaktion: Beginn der katalytischen Ära , 2003 .

[21]  S. Gibson,et al.  The Pauson-Khand reaction: the catalytic age is here! , 2003, Angewandte Chemie.

[22]  V. Ratovelomanana-Vidal,et al.  SYNPHOS: a New Atropisomeric Diphosphine Ligand. From Laboratory-scale Synthesis to Scale-up Development , 2003 .

[23]  A. Riera,et al.  Design of new hemilabile (P, S) ligands for the highly diastereoselective coordination to alkyne dicobalt complexes: Application to the asymmetric intermolecular Pauson-Khand reaction , 2003 .

[24]  K. Kakiuchi,et al.  Rhodium-Catalyzed Intramolecular Aminocarbonylation of Aryl Halides Using Aldehydes as a Source of Carbon Monoxide , 2003 .

[25]  K. Takagi,et al.  Rhodium complex-catalyzed Pauson-Khand-type reaction with aldehydes as a CO source. , 2002, The Journal of organic chemistry.

[26]  J. Adrio,et al.  Pauson−Khand Reactions of Electron-Deficient Alkenes , 2002 .

[27]  B. Hanson.  Catalytic Pauson Khand and Related Cycloaddition Reactions , 2002 .

[28]  Martin A. Abraham,et al.  Clean solvents : alternative media for chemical reactions and processing , 2002 .

[29]  K. Takagi,et al.  Catalytic Pauson-Khand-type reaction using aldehydes as a CO source. , 2002, Organic letters.

[30]  S. Buchwald,et al.  Cobalt-phosphite-catalyzed asymmetric Pauson-Khand reaction. , 2002, The Journal of organic chemistry.

[31]  A. Chan,et al.  Synthesis of new chiral diphosphine ligand (BisbenzodioxanPhos) and its application in asymmetric catalytic hydrogenation , 2002 .

[32]  K. Kakiuchi,et al.  CO-transfer carbonylation reactions. A catalytic Pauson-Khand-type reaction of enynes with aldehydes as a source of carbon monoxide. , 2002, Journal of the American Chemical Society.

[33]  W. Crowe,et al.  Gamma-butyrolactone synthesis via catalytic asymmetric cyclocarbonylation. , 2001, Journal of the American Chemical Society.

[34]  K. Takagi,et al.  Iridium−Chiral Diphosphine Complex Catalyzed Highly Enantioselective Pauson-Khand-Type Reaction , 2000 .

[35]  B. K. Sung,et al.  Rhodium(I)-Catalyzed Asymmetric Intramolecular Pauson−Khand-Type Reaction , 2000 .

[36]  Kay M. Brummond,et al.  Recent Advances in the Pauson–Khand Reaction and Related [2+2+1] Cycloadditions , 2000 .

[37]  K. Hiroi,et al.  Catalytic use of chiral phosphine ligands in asymmetric Pauson–Khand reactions , 2000 .

[38]  K. Hiroi,et al.  Asymmetric catalytic Pauson–Khand reactions with chiral phosphine ligands: Dramatic effects of substituents in 1,6-enyne systems , 2000 .

[39]  S. Christie,et al.  Cobalt mediated cyclisations , 2000 .

[40]  R. Crabtree,et al.  Aldehyde Decarbonylation Catalysis under Mild Conditions , 1999 .

[41]  S. Buchwald,et al.  An Intramolecular Titanium-Catalyzed Asymmetric Pauson−Khand Type Reaction1 , 1999 .

[42]  Y. Chung.  Transition metal alkyne complexes: the Pauson–Khand reaction , 1999 .

[43]  S. Buchwald,et al.  Catalytic Asymmetric Cyclocarbonylation of Nitrogen-Containing Enynes. , 1999, The Journal of organic chemistry.

[44]  Eric N. Jacobsen,et al.  Comprehensive asymmetric catalysis , 1999 .

[45]  S. Ingate,et al.  THE ASYMMETRIC PAUSON-KHAND REACTION. A REVIEW , 1998 .

[46]  S. Buchwald,et al.  Highly Enantioselective Catalytic Pauson−Khand Type Formation of Bicyclic Cyclopentenones , 1996 .

[47]  S. Schreiber,et al.  Cobalt-Mediated Total Synthesis of (+)-Epoxydictymene , 1994 .

[48]  J. Suggs.  Isolation of a stable acylrhodium(III) hydride intermediate formed during aldehyde decarbonylation. Hydroacylation , 1978 .

[49]  M. I. Foreman,et al.  Organocobalt complexes. Part II. Reaction of acetylenehexacarbonyldicobalt complexes, (R1C2R2)Co2(CO)6, with norbornene and its derivatives , 1973 .

[50]  P. Pauson,et al.  A cobalt induced cleavage reaction and a new series of arenecobalt carbonyl complexes , 1971 .

[51]  J. Tsuji,et al.  Organic synthesis by means of noble metal compounds. XXXV. Novel decarbonylation reactions of aldehydes and acyl halides using rhodium complexes , 1968 .

[52]  E. Bergmann,et al.  Decarbonylation of aromatic carbonyl compounds catalyzed by rhodium complexes , 1967 .