Literature DB >> 20734992

Desymmetrization of meso-cyclic imides via enantioselective monohydrogenation.

Satoshi Takebayashi1, Jeremy M John, Steven H Bergens.   

Abstract

meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88-97% ee using trans-[Ru((R)-BINAP)(H)(2)((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.

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Year:  2010        PMID: 20734992     DOI: 10.1021/ja105783u

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


  8 in total

1.  Crystal structure of rac-3-hy-droxy-2-(p-tol-yl)-2,3,3a,4,7,7a-hexa-hydro-1H-4,7-methano-isoindol-1-one.

Authors:  Mehmet Aslantaş; Cumali Çelik; Ömer Çelik; Arzu Karayel
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-02-04

2.  A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines.

Authors:  Yiping Shi; Paul C J Kamer; David J Cole-Hamilton; Michelle Harvie; Emma F Baxter; Kate J C Lim; Peter Pogorzelec
Journal:  Chem Sci       Date:  2017-08-08       Impact factor: 9.825

3.  Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides.

Authors:  Waldemar Schilling; Yu Zhang; Daniel Riemer; Shoubhik Das
Journal:  Chemistry       Date:  2019-12-05       Impact factor: 5.236

4.  Hydrogenative Depolymerization of Nylons.

Authors:  Amit Kumar; Niklas von Wolff; Michael Rauch; You-Quan Zou; Guy Shmul; Yehoshoa Ben-David; Gregory Leitus; Liat Avram; David Milstein
Journal:  J Am Chem Soc       Date:  2020-08-11       Impact factor: 15.419

5.  Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles.

Authors:  Zhe Chang; Jialin Huang; Si Wang; Geshuyi Chen; Heng Zhao; Rui Wang; Depeng Zhao
Journal:  Nat Commun       Date:  2021-07-15       Impact factor: 14.919

6.  Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions.

Authors:  Jose R Cabrero-Antonino; Rosa Adam; Veronica Papa; Mattes Holsten; Kathrin Junge; Matthias Beller
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

7.  Multifaceted catalytic hydrogenation of amides via diverse activation of a sterically confined bipyridine-ruthenium framework.

Authors:  Takashi Miura; Masayuki Naruto; Katsuaki Toda; Taiki Shimomura; Susumu Saito
Journal:  Sci Rep       Date:  2017-05-16       Impact factor: 4.379

Review 8.  Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen.

Authors:  Jose R Cabrero-Antonino; Rosa Adam; Veronica Papa; Matthias Beller
Journal:  Nat Commun       Date:  2020-08-04       Impact factor: 14.919

  8 in total

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