Catalyzed vinylogous Mukaiyama aldol reactions with controlled enantio- and diastereoselectivities.

In control: A new catalytic vinylogous Mukaiyama aldol reaction provides products with high diastereo- and enantioselectivities (up to 99 % de and ee; see scheme). The relative and absolute stereochemistry of a representative product was rigorously assigned by NMR and CD spectroscopies (measured and calculated), X-ray diffraction, and quantum-chemical calculations.

[1]  C. Bolm,et al.  Synthesis and Use of Chiral Sulfoximines , 2009 .

[2]  C. Curti,et al.  Further Uses of Pyrrole‐Based Dienoxysilane Synthons: A Full Aldol Approach to Azabicyclo[x.2.1]alkane Systems , 2008 .

[3]  K. Tatsuta,et al.  Asymmetric Vinylogous Mukaiyama Aldol Reactions Using Vinylketene N,O-Acetals in Total Syntheses of Natural Products , 2008 .

[4]  J. Sedelmeier,et al.  C1-symmetric oxazolinyl sulfoximines as ligands in copper-catalyzed asymmetric mukaiyama aldol reactions. , 2008, Organic letters.

[5]  M. Kalesse,et al.  Oxazaborolidinone-promoted vinylogous Mukaiyama aldol reactions. , 2007, Organic letters.

[6]  G. E. Keck,et al.  A catalytic asymmetric vinylogous Mukaiyama aldol reaction. , 2007, Organic letters.

[7]  A. Marinetti,et al.  A Stereoselective Approach to 1,3‐Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control , 2007 .

[8]  I. Paterson,et al.  Total synthesis and stereochemical reassignment of (+)-dolastatin 19, a cytotoxic marine macrolide isolated from Dolabella auricularia , 2007 .

[9]  S. Denmark,et al.  Lewis base activation of Lewis acids: catalytic, enantioselective vinylogous aldol addition reactions. , 2007, The Journal of organic chemistry.

[10]  S. Lebreton,et al.  Total synthesis and structure revision of the marine metabolite palmerolide A. , 2007, Journal of the American Chemical Society.

[11]  C. Bolm,et al.  Catalytic Asymmetric Synthesis: Sections 2.1.1 ‐ 2.1.3 , 2007 .

[12]  Susumu Kobayashi,et al.  Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction. , 2007, Organic letters.

[13]  M. D. Rosa,et al.  The first organocatalytic addition of 2-trimethylsilyloxyfuran to carbonyl compounds: hydrogen-bond catalysis in γ-butenolides synthesis , 2006 .

[14]  J. Campagne,et al.  α,β‐Unsaturated δ‐Lactones from Copper‐Catalyzed Asymmetric Vinylogous Mukaiyama Reactions of Aldehydes: Scope and Mechanistic Insights , 2006 .

[15]  D. Romo,et al.  Diastereoselective, vinylogous mukaiyama aldol additions of silyloxy furans to cyclic ketones: annulation of butenolides and gamma-lactones. , 2006, Organic letters.

[16]  C. Bolm,et al.  Sulfoximines as ligands in copper-catalyzed asymmetric vinylogous Mukaiyama-type aldol reactions. , 2006, Organic letters.

[17]  S. Denmark,et al.  Lewis base activation of Lewis acids. Vinylogous aldol addition reactions of conjugated N,O-silyl ketene acetals to aldehydes. , 2006, Journal of the American Chemical Society.

[18]  C. Bolm,et al.  Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions. , 2005, Chemistry.

[19]  Scott E. Denmark,et al.  Katalytische enantioselektive vinyloge Aldolreaktionen , 2005 .

[20]  S. Denmark,et al.  Catalytic, enantioselective, vinylogous aldol reactions. , 2005, Angewandte Chemie.

[21]  C. Bolm,et al.  C(1)-symmetric sulfoximines as ligands in copper-catalyzed asymmetric Mukaiyama-type aldol reactions. , 2004, Angewandte Chemie.

[22]  Carsten Bolm Prof.,et al.  C1-Symmetric Sulfoximines as Ligands in Copper-Catalyzed Asymmetric Mukaiyama-Type Aldol Reactions† , 2004 .

[23]  C. Bolm,et al.  Sulfoximines: Synthesis and Catalytic Applications , 2004 .

[24]  S. Liras,et al.  Novel approach to the zaragozic acids. Enantioselective total synthesis of 6,7-dideoxysqualestatin H5. , 2002, The Journal of organic chemistry.

[25]  F Zanardi,et al.  The vinylogous aldol reaction: a valuable, yet understated carbon-carbon bond-forming maneuver. , 2000, Chemical reviews.

[26]  L. Battistini,et al.  The synthetic utility of furan-, pyrrole- and thiophene-based 2-silyloxy dienes , 2000 .

[27]  Davidr . Evans,et al.  C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Scope and Mechanism of Catalytic Enantioselective Aldol Additions of Enolsilanes to (Benzyloxy)acetaldehyde , 1999 .

[28]  Davidr . Evans,et al.  C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Scope and Mechanism of the Catalytic Enantioselective Aldol Additions of Enolsilanes to Pyruvate Esters , 1999 .

[29]  P. J. Taylor,et al.  The tautomerism of indazolinone in aqueous solution. A note on the ‘principle of vinylogy’ , 1996 .

[30]  G. Bernardinelli,et al.  The synthesis of (±)-cavernosine , 1987 .

[31]  S. Krishnamurthy.  The principle of vinylogy , 1982 .

[32]  R. C. Fuson.  The Principle of Vinylogy. , 1935 .