Water-compatible hydrogen-bond activation: a scalable and organocatalytic model for the stereoselective multicomponent aza-Henry reaction.

We thank the Spanish MICINN (FEDER) for financial support (CTQ2011-28417-C02-02) and CSIC for a JAE-PRE grant (F. C.-A.).

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

[2]  Keniti Yamada,et al.  ERSTE KATALYTISCHE ASYMMETRISCHE NITRO-MANNICH-REAKTION MIT EINEM NEUEN HETERODIMETALLKOMPLEX ALS KATALYSATOR , 1999 .

[3]  Shibasaki,et al.  The First Catalytic Asymmetric Nitro-Mannich-Type Reaction Promoted by a New Heterobimetallic Complex. , 1999, Angewandte Chemie.

[4]  J. Engberts,et al.  Understanding organic reactions in water: from hydrophobic encounters to surfactant aggregates. , 2002, Chemical communications.

[5]  M. Pirrung,et al.  Multicomponent reactions are accelerated in water. , 2004, Journal of the American Chemical Society.

[6]  Y. Takemoto,et al.  Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst. , 2004, Organic letters.

[7]  D. Chandler Interfaces and the driving force of hydrophobic assembly , 2005, Nature.

[8]  M. Pirrung,et al.  Aqueous medium effects on multi-component reactions , 2005 .

[9]  M. Finn,et al.  "On water": unique reactivity of organic compounds in aqueous suspension. , 2005, Angewandte Chemie.

[10]  Raquel P. Herrera,et al.  Phase-transfer-catalyzed asymmetric aza-henry reaction using N-carbamoyl imines generated in situ from α-amido sulfones , 2005 .

[11]  W. Herrmann,et al.  Aqueous-Phase Organometallic Catalysis: Concepts and Applications , 2005 .

[12]  C. Palomo,et al.  Catalytic enantioselective aza-Henry reaction with broad substrate scope. , 2005, Journal of the American Chemical Society.

[13]  P. Dawson,et al.  Nucleophilic catalysis of oxime ligation. , 2006, Angewandte Chemie.

[14]  Yujiro Hayashi Prof. In Water or in the Presence of Water , 2006 .

[15]  Y. Hayashi In water or in the presence of water? , 2006, Angewandte Chemie.

[16]  Giovanni Muncipinto,et al.  Short synthesis of skeletally and stereochemically diverse small molecules by coupling petasis condensation reactions to cyclization reactions. , 2006, Angewandte Chemie.

[17]  P. Schreiner,et al.  Hydrophobic amplification of noncovalent organocatalysis. , 2006, Chemical communications.

[18]  R. Breinbauer Organic Reactions in Water. Principles, Strategies, and Applications , 2007 .

[19]  Robert Vácha,et al.  Water surface is acidic , 2007, Proceedings of the National Academy of Sciences.

[20]  U. Lindstrm,et al.  Organic Reactions in Water , 2007 .

[21]  Yousung Jung,et al.  On the Theory of Organic Catalysis "on Water" , 2007 .

[22]  S. Kobayashi Asymmetric catalysis in aqueous media , 2007 .

[23]  M. Snapper,et al.  Catalytic asymmetric alkylations of ketoimines. Enantioselective synthesis of N-substituted quaternary carbon stereogenic centers by Zr-catalyzed additions of dialkylzinc reagents to aryl-, alkyl-, and trifluoroalkyl-substituted ketoimines. , 2008, Journal of the American Chemical Society.

[24]  A. Linden,et al.  Asymmetric aza-Henry reaction under phase transfer catalysis: an experimental and theoretical study. , 2008, Journal of the American Chemical Society.

[25]  P. Ball Water as an active constituent in cell biology. , 2008, Chemical reviews.

[26]  Arkadi Vigalok,et al.  Highly efficient organic reactions "on water", "in water", and both. , 2008, Angewandte Chemie.

[27]  G. Richmond,et al.  Integration or segregation: how do molecules behave at oil/water interfaces? , 2008, Accounts of chemical research.

[28]  E. Jacobsen,et al.  Scaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acids , 2009, Nature.

[29]  M. Raj,et al.  Organocatalytic reactions in water. , 2009, Chemical communications.

[30]  J. Paradowska,et al.  Catalysts based on amino acids for asymmetric reactions in water. , 2009, Angewandte Chemie.

[31]  Alicia Sántos-Expósito,et al.  Lewis base-catalyzed three-component Strecker reaction on water. An efficient manifold for the direct alpha-cyanoamination of ketones and aldehydes. , 2009, Chemical communications.

[32]  Raquel P. Herrera,et al.  Catalytic Enantioselective Aza-Henry Reactions , 2009 .

[33]  K. Nagasawa,et al.  Enantioselective Aza‐Henry Reaction with Acyclic Guanidine‐Thiourea Bifunctional Organocatalyst , 2009 .

[34]  Water in Stereoselective Organocatalytic Reactions , 2009 .

[35]  P. Schreiner,et al.  (Thio)urea organocatalysis--what can be learnt from anion recognition? , 2009, Chemical Society reviews.

[36]  Joanna Paradowska,et al.  Aminosäuren als Katalysatoren für asymmetrische Umsetzungen in Wasser , 2009 .

[37]  K. Vasuki Multi-Component Reactions in Water , 2009 .

[38]  J. Szostak,et al.  Chemoselective Multicomponent One-Pot Assembly of Purine Precursors in Water , 2010, Journal of the American Chemical Society.

[39]  J. Beattie,et al.  The mechanism of on-water catalysis. , 2010, Chemistry.

[40]  A. Coyne,et al.  Water: nature's reaction enforcer--comparative effects for organic synthesis "in-water" and "on-water". , 2010, Chemical reviews.

[41]  E. Jacobsen,et al.  Enantioselective thiourea-catalyzed cationic polycyclizations. , 2010, Journal of the American Chemical Society.

[42]  Julian Tirado-Rives,et al.  Quantum mechanical/molecular mechanical modeling finds Diels-Alder reactions are accelerated less on the surface of water than in water. , 2010, Journal of the American Chemical Society.

[43]  M. Rueping,et al.  Asymmetric Brønsted acid catalysis in aqueous solution , 2010 .

[44]  K. Jørgensen,et al.  Squaramides: bridging from molecular recognition to bifunctional organocatalysis. , 2011, Chemistry.

[45]  A. Theberge,et al.  Investigation of "on water" conditions using a biphasic fluidic platform. , 2012, Angewandte Chemie.

[46]  P. Liu,et al.  Highly enantioselective nitro-Mannich reaction catalyzed by cinchona alkaloids and N-benzotriazole derived ammonium salts. , 2012, Organic letters.

[47]  M. Simon,et al.  Green chemistry oriented organic synthesis in water. , 2012, Chemical Society reviews.

[48]  D. Dixon,et al.  A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones. , 2012, Organic letters.

[49]  D. Du,et al.  Enantioselective Aza‐Henry Reaction of Imines Bearing a Benzothiazole Moiety Catalyzed by a Cinchona‐Based Squaramide , 2013 .

[50]  Adam Noble,et al.  Nitro-Mannich reaction. , 2013, Chemical reviews.