Nuno Maulide

Publications of Nuno Maulide

• Sulfoxide-mediated Umpolung of alkali halide salts.

  Authors: Sebastian Klimczyk, Xueliang Huang, Christophe Farès, Nuno Maulide

  Organic & biomolecular chemistry. 06/2012; 10(22):4327-9.

  A new protocol for the direct two-electron oxidative Umpolung of alkali halide salts is reported. This procedure, relying on the use of a commercially available sulfoxide as the oxidant, allows theA new protocol for the direct two-electron oxidative Umpolung of alkali halide salts is reported. This procedure, relying on the use of a commercially available sulfoxide as the oxidant, allows the electrophilic halogenation of carbonyl compounds as well as halolactonisation reactions to proceed from the corresponding sodium salts, at room temperature and under mild conditions.

• Intramolecular redox-triggered ch functionalization.

  Authors: Igor D Jurberg, Bo Peng, Eckhard Wöstefeld, Maximilian Wasserloos, Nuno Maulide

  Angewandte Chemie (International ed. in English). 02/2012; 51(8):1950-3.

  Sacrifice for the team: A one-pot method achieves remote functionalization at the α-position of an amine moiety through the sacrificial reduction of a neighboring group. The process takes advantageSacrifice for the team: A one-pot method achieves remote functionalization at the α-position of an amine moiety through the sacrificial reduction of a neighboring group. The process takes advantage of an intramolecular redox reaction, thereby avoiding the need for any external oxidants. This method was applied to a concise five-step total synthesis of indolizidine 167B.

• Total synthesis and structural revision of the piperarborenines: when photochemistry meets ch activation.

  Authors: Frédéric Frébault, Nuno Maulide

  Angewandte Chemie (International ed. in English). 02/2012; 51(12):2815-7.

  Activate and reiterate: The activation of C(sp(3) )H bonds is a highly desirable transformation because molecular complexity can be increased at the expense of the most simple and readily availableActivate and reiterate: The activation of C(sp(3) )H bonds is a highly desirable transformation because molecular complexity can be increased at the expense of the most simple and readily available organic linkage. In recent contributions this approach was used for coupling reactions with small all-carbon rings, as exemplified by the sequential CH activation steps in an elegant total synthesis of the piperarborenines (see scheme; DG=directing group).

• Catalytic asymmetric diastereodivergent deracemization.

  Authors: Marco Luparia, Maria Teresa Oliveira, Davide Audisio, Frédéric Frébault, Richard Goddard, Nuno Maulide

  Angewandte Chemie (International ed. in English). 11/2011; 50(52):12631-5.

  Your wish is my command: Deracemization is a powerful strategy wherein a racemate is converted into a 100 % yield of a single enantiopure product. A new concept in catalytic deracemization isYour wish is my command: Deracemization is a powerful strategy wherein a racemate is converted into a 100 % yield of a single enantiopure product. A new concept in catalytic deracemization is presented, in which a racemate with n stereogenic elements can be selectively converted into each one of 2(m) (m = number of chiral centers of the product) different enantiopure products, by simple tuning of the reaction conditions.

• Revisiting keteniminium salts: more than the nitrogen analogs of ketenes.

  Authors: Claire Madelaine, Viviana Valerio, Nuno Maulide

  Chemistry, an Asian journal. 06/2011; 6(9):2224-39.

  Keteniminium salts are powerful electrophilic heterocumulene reagents well-known for their selectivity and stereocontrol in [2+2] cycloadditions to olefins and carbonyl derivatives. Furthermore, theyKeteniminium salts are powerful electrophilic heterocumulene reagents well-known for their selectivity and stereocontrol in [2+2] cycloadditions to olefins and carbonyl derivatives. Furthermore, they are readily accessible from stable and simple precursors under a variety of different conditions. Herein, we present the chemistry of keteniminium salts with the hindsight of time, describe preparation methods, recent [2+2] chemistry, mechanistic studies, and assorted applications that significantly extend the scope of utility of these unique electrophilic heterocumulenes.

• Sulfoxide-mediated α-arylation of carbonyl compounds.

  Authors: Xueliang Huang, Nuno Maulide

  Journal of the American Chemical Society. 06/2011; 133(22):8510-3.

  A novel sulfoxide-mediated α-arylation of carbonyl compounds is reported. This reaction proceeds under very mild conditions at room temperature and does not require any transition-metal promoter orA novel sulfoxide-mediated α-arylation of carbonyl compounds is reported. This reaction proceeds under very mild conditions at room temperature and does not require any transition-metal promoter or catalyst.

• Steering reaction pathways: from benzyl Claisen rearrangements to powerful ionic shifts.

  Authors: Viviana Valerio, Claire Madelaine, Nuno Maulide

  Chemistry (Weinheim an der Bergstrasse, Germany). 03/2011; 17(17):4742-5.

• A direct ylide transfer to carbonyl derivatives and heteroaromatic compounds.

  Authors: Xueliang Huang, Richard Goddard, Nuno Maulide

  Angewandte Chemie (International ed. in English). 10/2010; 49(47):8979-83.

• A Concise Access to 3-Substituted 2-Pyrones.

  Authors: Frédéric Frébault, Maria Teresa Oliveira, Eckhard Wöstefeld, Nuno Maulide

  The Journal of organic chemistry. 10/2010;

  The development of a modular synthesis of 3-substituted-2-pyrones is described. The attainment of this strategy hinges on a new electrophilic pyrone derivative which can be readily prepared on aThe development of a modular synthesis of 3-substituted-2-pyrones is described. The attainment of this strategy hinges on a new electrophilic pyrone derivative which can be readily prepared on a multigram scale and which performs very competently in metal-catalyzed cross-coupling reactions with a variety of nucleophiles.

• A versatile and stereoselective synthesis of functionalized cyclobutenes.

  Authors: Frédéric Frébault, Marco Luparia, Maria Teresa Oliveira, Richard Goddard, Nuno Maulide

  Angewandte Chemie (International ed. in English). 08/2010; 49(33):5672-6.

• Unexpected electrophilic rearrangements of amides: a stereoselective entry to challenging substituted lactones.

  Authors: Claire Madelaine, Viviana Valerio, Nuno Maulide

  Angewandte Chemie (International ed. in English). 02/2010; 49(9):1583-6.

• Stereoselective, Dual-Mode Ruthenium-Catalyzed Ring Expansion of Alkynylcyclopropanols.

  Authors: Barry M Trost, Jia Xie, Nuno Maulide

  Journal of the American Chemical Society. 01/2009;

  A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylideneA novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or beta-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic transition metals.

• Ruthenium-Catalyzed Cross-Coupling of Tertiary Propargyl Alcohols with omega-Alkynenitriles: A Regio- and Stereoselective Surrogate for an Aldol Condensation.

  Authors: Barry M Trost, Nuno Maulide, Michael T Rudd

  Journal of the American Chemical Society. 01/2009;

  A novel catalytic alkyne cross-coupling reaction is reported which connects tertiary propargyl alcohols with omega-alkynylnitriles with perfect atom economy. This remarkable process generates highlyA novel catalytic alkyne cross-coupling reaction is reported which connects tertiary propargyl alcohols with omega-alkynylnitriles with perfect atom economy. This remarkable process generates highly functionalized, stereodefined dienones that are formal aldol products in a single step. Moreover, the specificity of the cyano substituent for this reaction demonstrates the unique and somewhat underappreciated properties of that functional group.

• A ruthenium-catalyzed, atom-economical synthesis of nitrogen heterocycles.

  Authors: Barry M Trost, Nuno Maulide, Robert C Livingston

  Journal of the American Chemical Society. 01/2009; 130(49):16502-3.