Literature DB >> 17263544

General asymmetric hydrogenation of alpha-branched aromatic ketones catalyzed by TolBINAP/DMAPEN-ruthenium(II) complex.

Noriyoshi Arai1, Hirohito Ooka, Keita Azuma, Toshio Yabuuchi, Nobuhito Kurono, Tsutomu Inoue, Takeshi Ohkuma.   

Abstract

[reaction: see text] A catalyst system consisting of RuCl2[(S)-tolbinap][(R)-dmapen] and t-C4H9OK in 2-propanol effects asymmetric hydrogenation of arylglyoxal dialkylacetals to give the alpha-hydroxy acetals in up to 98% ee. Hydrogenation of racemic alpha-amidopropiophenones under dynamic kinetic resolution predominantly gives the syn alcohols in up to 99% ee and >98% de, while the reaction of racemic bezoin methyl ether gives the anti alcohols in excellent stereoselectivity.

Entities:  

Year:  2007        PMID: 17263544     DOI: 10.1021/ol070125+

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Catalytic nucleophilic glyoxylation of aldehydes.

Authors:  Kimberly M Steward; Jeffrey S Johnson
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

Review 3.  Asymmetric hydrogenation of ketones: tactics to achieve high reactivity, enantioselectivity, and wide scope.

Authors:  Takeshi Ohkuma
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2010       Impact factor: 3.493

4.  A Rh(II)-catalyzed multicomponent reaction by trapping an α-amino enol intermediate in a traditional two-component reaction pathway.

Authors:  Shunying Liu; Wenfeng Yao; Yuan Liu; Qinghua Wei; Jianghui Chen; Xiang Wu; Fei Xia; Wenhao Hu
Journal:  Sci Adv       Date:  2017-03-08       Impact factor: 14.136

  4 in total

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