Literature DB >> 24555736

Copper-catalyzed enantioselective formal hydroamination of oxa- and azabicyclic alkenes with hydrosilanes and hydroxylamines.

Yuya Miki1, Koji Hirano, Tetsuya Satoh, Masahiro Miura.   

Abstract

A CuCl/(R,R)-Ph-BPE-catalyzed enantioselective formal hydroamination of oxa- and azabicyclic alkenes with polymethylhydrosiloxane (PMHS) and O-benzoylhydroxylamines has been developed. The efficient and stereoselective net addition of hydrogen and nitrogen atoms provides the corresponding optically active oxa- and azanorbornenyl- and -norbornanylamines in good yields and good enantiomeric ratios.

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Year:  2014        PMID: 24555736     DOI: 10.1021/ol5003219

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


  17 in total

1.  A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-12       Impact factor: 15.336

Review 2.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

3.  Versatile Homoallylic Boronates by Chemo-, SN 2'-, Diastereo- and Enantioselective Catalytic Sequence of Cu-H Addition to Vinyl-B(pin)/Allylic Substitution.

Authors:  Jaehee Lee; Sebastian Torker; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-20       Impact factor: 15.336

4.  Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

Authors:  R J Van Hoveln; S C Schmid; M Tretbar; C T Buttke; J M Schomaker
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

5.  Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes.

Authors:  Sheng Feng; Hua Hao; Peng Liu; Stephen L Buchwald
Journal:  ACS Catal       Date:  2019-11-21       Impact factor: 13.084

6.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

7.  Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones.

Authors:  Yang Yang; Ian B Perry; Gang Lu; Peng Liu; Stephen L Buchwald
Journal:  Science       Date:  2016-06-09       Impact factor: 47.728

Review 8.  Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.

Authors:  Michael T Pirnot; Yi-Ming Wang; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

9.  Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination.

Authors:  Dawen Niu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-07-21       Impact factor: 15.419

10.  Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach.

Authors:  Yi-Ming Wang; Nicholas C Bruno; Ángel L Placeres; Shaolin Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-08-12       Impact factor: 15.419

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