Thioether containing ligands for asymmetric allylic substitution reactions

Abstract This review covers reports in the literature on the use of thioether ligands in Pd-catalysed asymmetric allylic substitution reactions from 1996 to June 2006. In the first section, we will cover the results using (S,S)-homo and (S,S)-heterodonor ligands. In the next section, we will present the results using heterodonor (S,X)-ligands, emphasizing the results obtained with (S,N)- and (S,P)-donor ligands. We also discuss any reported mechanistic aspects according to the allylic substitution results.

[1]  D. S. James,et al.  Origins of Enantioselectivity with Nitrogen-Sulfur Chelate Ligands in Palladium-Catalyzed Allylic Substitution. , 1999, The Journal of organic chemistry.

[2]  B. Trost,et al.  Asymmetric Transition Metal-Catalyzed Allylic Alkylations. , 1996, Chemical reviews.

[3]  H. Nakano,et al.  Novel chiral xylofuranose-based phosphinooxathiane and phosphinooxazinane ligands for palladium-catalyzed asymmetric allylations , 2003 .

[4]  K. Orrell NMR studies of the dynamic stereochemistry of sulphur and selenium complexes of platinum , 1989 .

[5]  C. Claver,et al.  Modular furanoside phosphite ligands for asymmetric Pd-catalyzed allylic substitution. , 2001, The Journal of organic chemistry.

[6]  Howard C. Clark,et al.  The trans-influence: its measurement and significance , 1973 .

[7]  P. Pregosin,et al.  New Chiral N,S-Ligands Based on Oxazoline−Thioglucose Donors. Palladium(II)-Catalyzed Enantioselective Allylic Alkylation , 1998 .

[8]  S. Medici,et al.  Binaphthalene-templated N,S- and N,P-heterobidentate ligands with an achiral oxazoline pendant: Synthesis and assessment in asymmetric catalysis , 2003 .

[9]  E. Álvarez,et al.  C2-Symmetric bis-thioglycosides as new ligands for palladium-catalyzed allylic substitutions , 2003 .

[10]  H. Nakano,et al.  Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinooxathiane ligands. , 2001, The Journal of organic chemistry.

[11]  C. Claver,et al.  Furanoside thioether-phosphinite ligands for Pd-catalyzed asymmetric allylic substitution reactions : Scope and limitations , 2006 .

[12]  Yong‐Gui Zhou,et al.  Enantioselective palladium catalyzed allylic substitution with chiral thioether derivatives of ferrocenyl-oxazoline and the role of planar chirality in this reaction , 1998 .

[13]  T. Tu,et al.  Trans Effect of Different Coordinated Atoms of Planar Chiral Ferrocene Ligands with the Same Backbone in Palladium−Catalyzed Allylic Substitutions , 2003 .

[14]  C. Claver,et al.  Furanoside thioetherphosphinite ligands for Pd-catalyzed asymmetric allylic substitution reactions , 2005 .

[15]  C. Claver,et al.  Palladium-diphosphite catalysts for the asymmetric allylic substitution reactions. , 2005, The Journal of organic chemistry.

[16]  James D. Osborne,et al.  The synthesis of new planar chiral heterobidentate chelate ligands for asymmetric catalysis , 2005 .

[17]  K. Ahn,et al.  Synthesis of chiral 1′-substituted oxazolinylferrocenes as chiral ligands for Pd-catalyzed allylic substitution reactions , 1999 .

[18]  Huilin Chen,et al.  Chiral ferrocene-based phosphine-imine and sulfur-imine ligands for palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl esters , 2004 .

[19]  C. Claver,et al.  Furanoside thioether–phosphinite ligands for Rh-catalyzed asymmetric hydrosilylation of ketones , 2005 .

[20]  A. Pfaltz,et al.  PhosphinooxazolinesA New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis , 2000 .

[21]  A. Masdeu-Bultó Chiral thioether ligands: coordination chemistry and asymmetric catalysis , 2003 .

[22]  E. Álvarez,et al.  Highly diastereoselective formation of C2-symmetric bis-thioglycoside Pd(II) complexes: the role of the exo anomeric effect. , 2004, Chemical communications.

[23]  Jie Sun,et al.  Novel N,S- and N,Se-planar chiral [2,2]paracyclophane ligands: synthesis and application in Pd-catalyzed allylic alkylation , 2000 .

[24]  C. Claver,et al.  Homogeneous catalysis with transition metal complexes containing sulfur ligands , 1999 .

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

[26]  M. Shi,et al.  Palladium-catalyzed asymmetric allylic substitutions by axially chiral P,S-, S,S-, and S,O-heterodonor ligands with a binaphthalene framework , 2004 .

[27]  C. Claver,et al.  New phosphite-oxazoline ligands for efficient Pd-catalyzed substitution reactions. , 2005, Journal of the American Chemical Society.

[28]  Yoshio Suzuki,et al.  (S)-Proline-derived new chiral ligands with phosphino, organosulfur or organoselenenyl functionality as an enantiocontrollable coordinating element , 1999 .

[29]  Davidr . Evans,et al.  Application of Chiral Mixed Phosphorus/Sulfur Ligands to Palladium-Catalyzed Allylic Substitutions , 2000 .

[30]  A. Albinati,et al.  Palladium .pi.-Allyl Chemistry of New P,S Bidentate Ligands. Selective but Variable Dynamics in the Isomerization of the .eta.3-C3H5 and .eta.3-PhCHCHCHPh .pi.-Allyl Ligands , 1995 .

[31]  L. Bernardi,et al.  Chiral oxazoline-1,3-dithianes : new effective nitrogen-sulfur donating ligands in asymmetric catalysis , 2005 .

[32]  N. Culeddu,et al.  Enantiomerically pure pyridine and 2,2'-bipyridine thioethers: new N-S chiral ligands for asymmetric catalysis. Palladium catalyzed allylic alkylation , 1999 .

[33]  R. Nesper,et al.  Chiral P,S-Ligands Based on β-d-Thioglucose Tetraacetate. Palladium(II) Complexes and Allylic Alkylation , 1996 .

[34]  L. Wessjohann,et al.  Microwave-accelerated asymmetric allylations using cysteine derived oxazolidine and thiazolidine palladium complexes , 2005 .

[35]  Jun Hee Lee,et al.  Preparation of pseudo-C2-symmetric P,S-hybrid ferrocenyl ligand and its application to some asymmetric reactions , 2003 .

[36]  R. Kellogg,et al.  Chiral nonracemic pyridine thiols and thioethers applied in palladium-catalyzed allylic substitution. An example of near-perfect enantioselection , 1998 .

[37]  B. Trost DESIGNING A RECEPTOR FOR MOLECULAR RECOGNITION IN A CATALYTIC SYNTHETIC REACTION : ALLYLIC ALKYLATION , 1996 .

[38]  Lucie Routaboul,et al.  New ferrocenyl P,S and S,S ligands for asymmetric catalysis , 2005 .

[39]  H. Nakano,et al.  Novel and efficient chiral sulfideoxathiane ligands for palladium-catalyzed asymmetric allylic alkylationElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b2/b211031h/ , 2003 .

[40]  A. Chan,et al.  Easily accessible ferrocenyl N-P/S type ligands and their applications in asymmetric allylic substitutions , 2006 .

[41]  O. García Mancheño,et al.  Chiral copper complexes of phosphino sulfenyl ferrocenes as efficient catalysts for enantioselective formal Aza Diels-Alder reactions of N-sulfonyl imines. , 2004, Journal of the American Chemical Society.

[42]  A. Albinati,et al.  CHIRAL PHOSPHITO-THIOETHER COMPLEXES OF PALLADIUM(0). COMMENTS ON THE PD, RH, AND IR REGIO-AND-ENANTIOSELECTIVE ALLYLIC ALKYLATIONS OF PHCH=CHCH(OAC)R , R = H, ME, ET , 1999 .

[43]  L. Wessjohann,et al.  First Generation Cysteine‐ and Methionine‐Derived Oxazolidine and Thiazolidine Ligands for Palladium‐Catalyzed Asymmetric Allylations , 2004 .

[44]  H. Takada,et al.  Catalytic diastereoselective sulfimidation of diaryl sulfides and application of chiral sulfimides to asymmetric allylic alkylation. , 2000, Chirality.

[45]  C. Claver,et al.  Asymmetric hydrogenation of prochiral olefins catalysed by furanoside thioether-phosphinite Rh(I) and Ir(I) complexes. , 2005, Dalton transactions.

[46]  F. Lahoz,et al.  Persulfurated complexes of palladium(II) and platinum(II) with fluorinated aryl-thiolates. X-ray structure of [Pt(SC6F5)2(CH3SCH(CH3)CH(CH3)SCH3)] , 1998 .

[47]  C. Claver,et al.  Synthesis and Coordination Chemistry of Novel Chiral P,S-Ligands with a Xylofuranose Backbone: Use in Asymmetric Hydroformylation and Hydrogenation , 2000 .

[48]  M. Shi,et al.  Axially chiral P,S-heterodonor ligands with a binaphthalene framework for palladium-catalyzed asymmetric allylic substitutions: experimental investigation on the reversal of enantioselectivity between different alkyl groups on sulfur atom , 2004 .

[49]  G. Pirri,et al.  BINAPS - An axially chiral P,S-heterodonor ligand for asymmetric catalysis based on binaphthalene backbone , 2001 .

[50]  R. Braga,et al.  Efficient synthesis of chiral beta-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation. , 2005, The Journal of organic chemistry.

[51]  S. You,et al.  Role of planar chirality of S,N- and P,N-ferrocene ligands in palladium-catalyzed allylic substitutions. , 2002, The Journal of organic chemistry.

[52]  D. S. James,et al.  Sulfur–imine mixed donor chelate ligands for asymmetric catalysis: enantioselective allylic alkylation , 1998 .

[53]  P. Guiry,et al.  The Development of Bidentate P,N Ligands for Asymmetric Catalysis , 2004 .

[54]  Davidr . Evans,et al.  Chiral Mixed Phosphorus/Sulfur Ligands for Palladium-Catalyzed Allylic Alkylations and Aminations. , 1999, The Journal of organic chemistry.

[55]  L. Bernardi,et al.  Synthesis and Chemistry of New Central and Planar Chiral Sulfur-Containing Ferrocenyl Compounds , 2005 .

[56]  Elżbieta Wojaczyńska,et al.  Chiral pyrrolidine thioethers: effective nitrogen–sulfur donating ligands in palladium-catalyzed asymmetric allylic alkylations , 2004 .

[57]  Yoshio Suzuki,et al.  Organosulfur Functionality as an Alternative Enantiocontrollable Coordinating Element in Chiral Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylations , 1999 .

[58]  A. Bacchi,et al.  Enantiomerically pure 1-(2-methoxy-1-naphthyl) and 1-(2-methylthio-1-naphthyl)isoquinoline: two new axially chiral NO and NS ligands for asymmetric catalysis , 1999 .

[59]  A. Pfaltz Chiral semicorrins and related nitrogen heterocycles as ligands in asymmetric catalysis , 1993 .

[60]  C. Claver,et al.  Thioether–phosphinite and diphosphinite ligands derived from d-xylose for the copper-catalyzed asymmetric 1,4-addition to 2-cyclohexenone , 2005 .

[61]  M. Paixão,et al.  New Aziridine Sulfide Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylation , 2004 .

[62]  N. Khiar,et al.  Sulfur–Sulfur‐Based Ligands Derived from D‐Sugars: Synthesis of PdII Complexes, Application in Palladium‐Catalyzed Allylic Alkylation for the Synthesis of Both Members of Enantiomer Pairs, and Structural Studies , 2006 .

[63]  T. Kida,et al.  NOVEL AXIAL CHIRAL SULFUR-OXAZOLINE LIGANDS WITH A BIPHENYL BACKBONE , 1999 .

[64]  J. Howard,et al.  Chiral ferrocenyl-oxazolines incorporating thioether units: effective ligands for palladium-catalysed allylic substitution , 1997 .

[65]  B. Trost,et al.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis. , 2003, Chemical reviews.

[66]  Jason P. Burke,et al.  Synthesis and application of chiral cyclopropane-based ligands in palladium-catalyzed allylic alkylation. , 2004, The Journal of organic chemistry.

[67]  A. Albinati,et al.  A New P,S-Chiral Auxiliary Derived from Thioglucose. X-ray Structure of a Palladium 1,3-Diphenylallyl Complex with a Strongly Rotated Allyl Ligand , 1996 .

[68]  L. Flores-Santos,et al.  Chiral S , S -donor ligands in palladium-catalysed allylic alkylation , 2001 .