Discovery of indium complexes as water-tolerant Lewis acids.

The work on development of organic reactions that are tolerant to air and moisture, especially that of carbon-carbon bond forming reactions, had only started in the early 1990s. Our laboratory had approached this subject when it was still in its infancy and had developed methodologies for that end. In this article, our decade of work on indium complexes as Lewis acids is summarised.

[1]  T. Loh,et al.  Catalytic enantioselective allylation of aldehydes via a moisture-tolerant chiral BINOL–In(III) complex , 2005 .

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[9]  C. Hartley.  New Applications of Indium Catalysts in Organic Synthesis , 2004 .

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[11]  T. Mukaiyama,et al.  Lithium Acetate Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate in a Dimethylformamide–H2O Solvent , 2003 .

[12]  T. Loh,et al.  Asymmetric Mannich-type reactions catalyzed by indium(III) complexes in ionic liquids , 2003 .

[13]  E. Juaristi,et al.  Reexamination of CeCl3 and InCl3 as activators in the diastereoselective Mukaiyama aldol reaction in aqueous media. , 2003, The Journal of organic chemistry.

[14]  Chao‐Jun Li,et al.  Direct formation of 2,4-disubstituted tetrahydropyranols in water mediated by an acidic solid resin , 2003 .

[15]  K. Manabe,et al.  Ligand-accelerated cadmium-catalyzed asymmetric allylation reactions in aqueous media. , 2003, Chirality.

[16]  K. Maruoka,et al.  Catalytic enantioselective allylation of ketones with novel chiral bis-titanium(IV) catalyst. , 2003, Chirality.

[17]  Satwinder Singh,et al.  Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols , 2002 .

[18]  Jason Gavenonis,et al.  A simple, reliable, catalytic asymmetric allylation of ketones. , 2002, Angewandte Chemie.

[19]  T. Loh,et al.  InCl(3)-catalyzed three-component asymmetric Mannich-type reaction in methanol. , 2002, Organic letters.

[20]  Chao‐Jun Li,et al.  Direct formation of tetrahydropyranols via catalysis in ionic liquid , 2002 .

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[24]  M. Kanai,et al.  A general catalytic allylation using allyltrimethoxysilane. , 2002, Journal of the American Chemical Society.

[25]  Y. Mori,et al.  Catalytic Use of a Boron Source for Boron Enolate Mediated Stereoselective Aldol Reactions in Water. , 2001, Angewandte Chemie.

[26]  T. Loh,et al.  InCl3-Catalyzed direct aldol reactions of glyoxylic acid monohydrate and glyoxylates with various ketones: scope and limitations , 2001 .

[27]  Takehisa Dewa,et al.  Enolization and Aldol Reactions of Ketone with a La3+-Immobilized Organic Solid in Water. A Microporous Enolase Mimic , 2001 .

[28]  Giebel,et al.  Cross-Linked Scandium-Containing Dendrimers: A New Class of Heterogeneous Catalysts. , 2000, Angewandte Chemie.

[29]  T. Loh,et al.  A catalytic enantioselective allylation reaction of aldehydes in an aqueous medium , 2000 .

[30]  T. Loh,et al.  Three Component Synthesis of β-Amino Carbonyl Compounds Using Indium Trichloride-Catalyzed One-pot Mannich-type Reaction in Water , 2000 .

[31]  Huang,et al.  Aldol reaction under solvent-free conditions: highly stereoselective synthesis of 1,3-amino alcohols , 2000, Organic letters.

[32]  T. Loh,et al.  An enantioselective indium-mediated allylation reaction of aldehydes and ketones in dichloromethane , 1999 .

[33]  T. Loh,et al.  An enantioselective allylation reaction of aldehydes in an aqueous medium , 1999 .

[34]  T. Loh,et al.  A Highly Enantioselective Indium-Mediated Allylation Reaction of Aldehydes , 1999 .

[35]  T. Loh,et al.  A simple and practical synthesis of α-trifluoromethylated alcohols in water , 1999 .

[36]  Chao‐Jun Li,et al.  Highly effective synthesis of 4-halo-tetrahydropyrans via a highly diastereoselective in situ Prins-type cyclization reaction , 1999 .

[37]  Shuj Kobayashi,et al.  Lewis Acid Catalysts Stable in Water. Correlation between Catalytic Activity in Water and Hydrolysis Constants and Exchange Rate Constants for Substitution of Inner-Sphere Water Ligands , 1998 .

[38]  T. Loh,et al.  Indium-trichloride catalyzed Michael reaction of silyl enol ethers with α,β-unsaturated carbonyl compounds under neat condition , 1998 .

[39]  Michael Arend,et al.  Modern Variants of the Mannich Reaction. , 1998, Angewandte Chemie.

[40]  R. Mahrwald,et al.  Highly Regioselective Lewis Acid-Mediated Aldol Additions at the More Encumbered α-Side of Unsymmetrical Ketones , 1998 .

[41]  T. Loh,et al.  Novel one-pot Mannich-type reaction in water: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters , 1998 .

[42]  D. Marton,et al.  MODERATE ENANTIOSELECTIVITY PROMOTED BY CYCLODEXTRINS IN THE Zn-BARBIER ALLYLATION REACTION OF ALDEHYDES IN AQUEOUS MEDIUM , 1998 .

[43]  T. Loh,et al.  A Highly Stereoselective Synthesis of β‐Trifluoromethylated Homoallylic Alchols in Water , 1997 .

[44]  G. Cao,et al.  Indium-trichloride catalyzed mukaiyama-aldol reaction in water: Solubility, aggregation and internal pressure effect , 1997 .

[45]  T. Loh,et al.  LANTHANOID TRIFLATE-PROMOTED INDIUM- OR ZINC-MEDIATED ALLYLATION OF AMINOALDEHYDE IN AQUEOUS MEDIA: STEREOSELECTIVE ROUTE TO ß-AMINOALCOHOLS , 1997 .

[46]  T. Loh,et al.  Indium trichloride-promoted tin-mediated carbonyl allylation in water: High simple diastereo- and diastereofacial selectivity , 1996 .

[47]  L. Paquette,et al.  Addition of Allylindium Reagents to Aldehydes Substituted at Cα or Cβ with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems , 1996 .

[48]  R. Nomura,et al.  Solvent-controlled addition of alkynyltins or allylic tins to aldehydes catalyzed by indium trichloride , 1995 .

[49]  Choon‐Hong Tan,et al.  Ytterbium trifluoromethanesulfonate [Yb(OTf)3] promoted indium mediated allylation reactions of carbonyl compounds in aqueous media , 1995 .

[50]  K. Hinkle,et al.  Synthesis of anti-Homoallylic Alcohols and Monoprotected 1,2-Diols through InCl3-Promoted Addition of Allylic Stannanes to Aldehydes , 1995 .

[51]  Shuj Kobayashi,et al.  Lanthanide triflates as water-tolerant Lewis acids. Activation of commercial formaldehyde solution and use in the aldol reaction of silyl enol ethers with aldehydes in aqueous media , 1994 .

[52]  Chao-Jun Li,et al.  Organometallic reactions in aqueous media with indium , 1991 .

[53]  G. Whitesides,et al.  Carbon-carbon bond formation in aqueous ethanol : diastereoselective transformation of unprotected carbohydrates to higher carbon sugars using allyl bromide and tin metal , 1991 .

[54]  Ronald Breslow,et al.  Hydrophobic Effects on Simple Organic Reactions in Water , 1991 .

[55]  Davidr . Evans,et al.  Stereoselective aldol reactions of chlorotitanium enolates. An efficient method for the assemblage of polypropionate-related synthons , 1991 .

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[58]  Kazuo Banno,et al.  New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride , 1974 .

[59]  Davidr . Evans,et al.  Synthetic applications of trimethylsilyl cyanide. Efficient synthesis of .beta.-aminomethyl alcohols , 1974 .

[60]  Davidr . Evans,et al.  New selective carbonyl blocking group. Regioselective protection of p-quinones , 1973 .