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Shinagawa-ku, Japan

Yin L.,University of Tokyo | Kanai M.,University of Tokyo | Shibasaki M.,Institute of Microbial Chemistry
Angewandte Chemie - International Edition | Year: 2011

Less metal wastes: The first catalytic, enantioselective intramolecular aryl-transfer reaction of aryl triflates to ketones has been developed (see scheme; R 1=R 2=aromatic and aliphatic). This method features overall practicality, including substrate stability and accessibility (protecting-group free) plus no need for the use of stoichiometric amounts of metals. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Lu G.,University of Tokyo | Yoshino T.,University of Tokyo | Morimoto H.,University of Tokyo | Matsunaga S.,University of Tokyo | Shibasaki M.,Institute of Microbial Chemistry
Angewandte Chemie - International Edition | Year: 2011

Now accessible: Sterically hindered vicinal tetrasubstituted carbon stereocenters, which are not accessible by asymmetric hydrogenation, were constructed by a catalytic asymmetric C-C bond formation (see scheme; Dpp=diphenylphosphinoyl). By changing the Group 2 metal center, stereodivergent access to α,β-tetrasubstituted α,β-diamino esters was realized. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Matsunaga S.,University of Tokyo | Matsunaga S.,Japan Science and Technology Agency | Shibasaki M.,Institute of Microbial Chemistry
Chemical Communications | Year: 2014

Cooperative catalysis has proven to be a powerful strategy for realizing high reactivity and selectivity in asymmetric transformations. A variety of cooperative asymmetric catalysts have been developed over the last two decades. In this feature article, recent advances from our research on cooperative asymmetric catalysis, focusing on dinuclear Schiff base catalysis, are described. Design of dinuclear Schiff base catalysts and their applications in several asymmetric C-C and C-N bond-forming reactions under simple proton transfer conditions with perfect atom-economy are discussed in detail. © 2014 The Royal Society of Chemistry. Source


Yazaki R.,Institute of Microbial Chemistry | Yazaki R.,University of Tokyo | Kumagai N.,Institute of Microbial Chemistry | Shibasaki M.,Institute of Microbial Chemistry
Journal of the American Chemical Society | Year: 2010

Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides under proton transfer conditions is described. Soft Lewis acid/hard Brønsted base cooperative catalysis is crucial for simultaneous activation of terminal alkynes and thioamides, affording the β-alkynylthioamides in a highly enantioselective manner. Control experiments suggested that the intermediate copper thioamide enolate can work as Brønsted base to drive the catalytic cycle via proton transfer. The divergent transformation of the thioamide functionality highlights the synthetic utility of the alkynylation products. © 2010 American Chemical Society. Source


Nitabaru T.,Institute of Microbial Chemistry | Nitabaru T.,University of Tokyo | Kumagai N.,Institute of Microbial Chemistry | Shibasaki M.,Institute of Microbial Chemistry
Angewandte Chemie - International Edition | Year: 2012

Battling the flu: Zanamivir (Relenza) is widely prescribed as an anti-influenza drug. It contains a vicinal amino alcohol, which is in an anti orientation, and is readily accessed by an anti-selective catalytic asymmetric nitroaldol (Henry) reaction promoted by a heterobimetallic complex (see scheme; PMB=p-methoxybenzyl). Additional synthetic manipulation of the nitroaldol product allowed the enantioselective synthesis of zanamivir. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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