Literature DB >> 16819850

Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py.

Hanmin Huang1, Tomoko Okuno, Kazuomi Tsuda, Masahiro Yoshimura, Masato Kitamura.   

Abstract

Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(pi-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10 000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions.

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Year:  2006        PMID: 16819850     DOI: 10.1021/ja062451a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  (R)-N,N'-Dimethyl-1,1'-binaphthyldiamine.

Authors:  Scott E Denmark; Pavel G Ryabchuk
Journal:  Organic Synth       Date:  2019-09-27

2.  Steric modulation of chiral biaryl diamines via Pd-catalyzed directed C-H arylation.

Authors:  Christopher C Scarborough; Richard I McDonald; Caroline Hartmann; Graham T Sazama; Ana Bergant; Shannon S Stahl
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

3.  Three-way switching in a cyanide-bridged [CoFe] chain.

Authors:  Norihisa Hoshino; Fumichika Iijima; Graham N Newton; Norifumi Yoshida; Takuya Shiga; Hiroyuki Nojiri; Akiko Nakao; Reiji Kumai; Youichi Murakami; Hiroki Oshio
Journal:  Nat Chem       Date:  2012-09-16       Impact factor: 24.427

4.  CH2 Linkage Effects on the Reactivity of Bis(aminophosphine)-Ruthenium Complexes for Selective Hydrogenation of Esters into Alcohols.

Authors:  Xiaolong Fang; Mingjun Sun; Jianwei Zheng; Bin Li; Linmin Ye; Xiaoping Wang; Zexing Cao; Hongping Zhu; Youzhu Yuan
Journal:  Sci Rep       Date:  2017-06-21       Impact factor: 4.379

5.  Ru/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to aliphatic aldehydes and α-ketoesters.

Authors:  Yasunori Yamamoto; Tomohiko Shirai; Momoko Watanabe; Kazunori Kurihara; Norio Miyaura
Journal:  Molecules       Date:  2011-06-17       Impact factor: 4.411

  5 in total

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