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By Takao Ikariya, Masakatsu Shibasaki

Masakatsu Shibasaki, Motomu Kanai, Shigeki Matsunaga, and Naoya Kumagai: Multimetallic Multifunctional Catalysts for uneven Reactions.- Takao Ikariya: Bifunctional transition metal-based molecular catalysts for uneven syntheses.- Chidambaram Gunanathan and David Milstein: Bond Activation by way of Metal-Ligand Cooperation: layout of ”Green” Catalytic Reactions in line with Aromatization-Dearomatization of Pincer Complexes.- Madeleine C. Warner, Charles P. Casey, and Jan-E. Bäckvall: Shvo’s Catalyst in Hydrogen move Reactions.- Noritaka Mizuno, Keigo Kamata, and Kazuya Yamaguchi: Liquid-Phase Selective Oxidation by means of Multimetallic lively websites of Polyoxometalate-Based Molecular Catalysts.- Pingfan Li and Hisashi Yamamoto: Bifunctional Acid Catalysts for natural Synthesis.- Jun-ichi Ito, Hisao Nishiyama: Bifunctional Phebox Complexes for uneven Catalysis.

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13 [57]. Further synthetic transformation of the chiral hydroxyamides provides chiral piperidinone derivatives which serve as important synthetic intermediates for a number of physiologically active chiral compounds including the antidepressant paroxetine. Similarly, readily accessible sym-glutar- or succinimides with the N-3,4-(OCH2O)C6H3 group undergo highly enantioselective hydrogenation via desymmetrization to give the corresponding hydroxyamides with excellent ee’s (Fig. 13) [58]. The present hydrogenation method would provide highly functionalized chiral hydroxyamides, which would otherwise require tedious multistep synthesis.

D’Augustin M, Palais L, Alexakis AJ (2005) Angew Chem Int Ed 44:1376 63. Fillion E, Wilsily A (2006) J Am Chem Soc 128:2774 64. Shintani R, Tsutsumi Y, Nagaosa M, Nishimura T, Hayashi T (2009) J Am Chem Soc 131:13588 65. Mita T, Sasaki K, Kanai M, Shibasaki M (2005) J Am Chem Soc 127:514 66. Fujimori I, Mita T, Maki K, Shiro M, Sato A, Furusho S, Kanai M, Shibasaki M (2007) Tetrahedron 63:5820 30 M. Shibasaki et al. 67. 68. 69. 70. 71. 72. 73. 74. 75. Tanaka Y, Kanai M, Shibasaki M (2008) J Am Chem Soc 130:6072 Sammis GM, Jacobsen EN (2003) J Am Chem Soc 125:4442 Sammis GM, Danjo H, Jacobsen EN (2004) J Am Chem Soc 126:9928 Mazet C, Jacobsen EN (2008) Angew Chem Int Ed 47:1762 Wang J, Li W, Liu Y, Chu Y, Lin L, Liu X, Feng X (2010) Org Lett 12:1280 Tanaka Y, Kanai M, Shibasaki M (2010) J Am Chem Soc 132:8862.

Thus, using enol silyl ethers as TMSNuc, transmetalation would produce 10 containing a rare earth metal enolate (Nuc ¼ enolate). If protonolysis of the silyl ether moiety of 10 is faster than that of the rare earth metal enolate, 11 containing activated enolate and proton both at the defined positions in a chiral multimetallic complex would be generated. Enantioselective protonation should proceed from 11, producing ketones 14 containing a-tertiary chiral center. The catalytic enantioselective protonation of prochiral enolates is a synthetically versatile reaction, but enantioselectivity is generally difficult to induce due to the extremely small size of proton [45–52].

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