Enantioselective Prévost and Woodward reactions using chiral hypervalent iodine(III): switchover of stereochemical course of an optically active 1,3-dioxolan-2-yl cation.

Optically active 1,3-dioxolan-2-yl cation intermediates were generated during enantioselective dioxyacetylation of alkene with chiral hypervalent iodine(III). Regioselective attack of a nucleophile toward the intermediate resulted in reversal of enantioselectivity of the dioxyacetylation.

[1]  T. Sugimura,et al.  Enantiodifferentiating endo-selective oxylactonization of ortho-alk-1-enylbenzoate with a lactate-derived aryl-λ3-iodane. , 2010, Angewandte Chemie.

[2]  K. Ishihara,et al.  Chiral hypervalent iodine-catalyzed enantioselective oxidative Kita spirolactonization of 1-naphthol derivatives and one-pot diastereo-selective oxidation to epoxyspirolactones , 2010 .

[3]  H. Okamoto,et al.  Quaternary Ammonium (Hypo)iodite Catalysis for Enantioselective Oxidative Cycloetherification , 2010, Science.

[4]  D. Lupton,et al.  The Discovery of Catalytic Enantioselective Polyvalent Iodine Mediated Reactions , 2010 .

[5]  K. Ishihara,et al.  Enantioselective Kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine(III) species. , 2010, Angewandte Chemie.

[6]  C. Chai,et al.  Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant. , 2010, Organic letters.

[7]  G. Zanoni,et al.  Synthesis and assignment of absolute configuration of the iridoid 9-deoxygelsemide. , 2010, Organic Letters.

[8]  James A. Lee,et al.  Ammonium-directed oxidation of cyclic allylic and homoallylic amines. , 2009, Journal of Organic Chemistry.

[9]  D. Cavagnat,et al.  Asymmetric hydroxylative phenol dearomatization through in situ generation of iodanes from chiral iodoarenes and m-CPBA. , 2009, Angewandte Chemie.

[10]  T. Sugimura,et al.  Asymmetric cycloetherification based on a chiral auxiliary for 4-acyloxy-1-butene substrates during oxidation with iodosylbenzene via a 1,3-dioxan-2-yl cation , 2009 .

[11]  V. B. Birman,et al.  Asymmetric oxidation of o-alkylphenols with chiral 2-(o-iodoxyphenyl)-oxazolines. , 2009, Organic letters.

[12]  Shauna M. Paradine,et al.  Catalytic Enantioselective α‐Oxysulfonylation of Ketones Mediated by Iodoarenes , 2008 .

[13]  Youlin Zeng,et al.  Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method. , 2008, The Journal of organic chemistry.

[14]  Chi‐Huey Wong,et al.  A concise and flexible synthesis of the potent anti-influenza agents tamiflu and tamiphosphor. , 2008, Angewandte Chemie.

[15]  E. Carreira,et al.  Synthesis and biological studies of 35-deoxy amphotericin B methyl ester. , 2008, Angewandte Chemie.

[16]  T. Dohi,et al.  A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols. , 2008, Angewandte Chemie.

[17]  D. Song,et al.  Palladium-catalyzed olefin dioxygenation. , 2008, Journal of the American Chemical Society.

[18]  T. Sugimura,et al.  Enantiodifferentiating tetrahydrofuranylation of but-3-enyl carboxylates using optically active hypervalent iodine(III) reagents via a 1,3-dioxan-2-yl cation intermediate , 2007 .

[19]  V. Zhdankin,et al.  Synthesis and oxidative reactivity of new chiral hypervalent iodine(V) reagents based on (S)-proline , 2006 .

[20]  B. Borhan,et al.  Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies. , 2006, The Journal of organic chemistry.

[21]  B. M. Pinto,et al.  A mild Pummerer-like reaction of carbohydrate-based selenoethers and thioethers involving linear ozonide acetates as putative intermediates. , 2006, Journal of the American Chemical Society.

[22]  A. Sudalai,et al.  NaIO4/LiBr-mediated diastereoselective dihydroxylation of olefins: a catalytic approach to the Prevost-Woodward reaction. , 2005, Organic letters.

[23]  O. Ramström,et al.  Solvent-dependent, kinetically controlled stereoselective synthesis of 3- and 4-thioglycosides. , 2005, The Journal of organic chemistry.

[24]  G. Boons,et al.  A general strategy for stereoselective glycosylations. , 2005, Journal of the American Chemical Society.

[25]  B. Borhan,et al.  One-pot regio- and stereoselective cyclization of 1,2,n-triols. , 2005, Journal of the American Chemical Society.

[26]  K. Park,et al.  Stereodivergent syntheses of anisomycin derivatives from D-tyrosine. , 2005, The Journal of organic chemistry.

[27]  G. Boons,et al.  Stereoselective glycosylation reactions with chiral auxiliaries. , 2005, Angewandte Chemie.

[28]  J. Y. Kim,et al.  Stereodivergent and regioselective synthesis of 3,4-cis- and 3,4-trans-pyrrolidinediols from alpha-amino acids. , 2004, Organic letters.

[29]  K. Miyamoto,et al.  Isolation, characterization, and reaction of activated iodosylbenzene monomer hydroxy(phenyl)iodonium ion with hypervalent bonding: supramolecular complex PhI+OH.18-crown-6 with secondary I...O interactions. , 2003, Journal of the American Chemical Society.

[30]  J. Giner,et al.  Synthesis of 2-methyl-D-erythritol via epoxy ester-orthoester rearrangement. , 2002, The Journal of organic chemistry.

[31]  O. Wiest,et al.  Chiral Hypervalent Organo‐Iodine(III) Compounds , 2001 .

[32]  W. Szarek,et al.  Iodine in carbohydrate chemistry. , 2000, Advances in carbohydrate chemistry and biochemistry.

[33]  B. Spingler,et al.  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis , 1998 .

[34]  Jean Rodriguez,et al.  Cohalogenation in Organic Synthesis , 1994 .

[35]  N. Zefirov,et al.  Iodosobenzene Tetrafluoroborate, Hexafluoroantimonate, and Hexafluorophosphate: Stable Electrophilic Hypervalent Iodine Reagents without Nucleophilic Ligands , 1989 .

[36]  C. Pittman,et al.  1,3-Dioxolan-2-ylium and related heterocyclic cations , 1972 .

[37]  R. Woodward,et al.  cis-Hydroxylation of a Synthetic Steroid Intermediate with Iodine, Silver Acetate and Wet Acetic Acid , 1958 .