Enantioselective Iridium-Catalyzed Allylic Amination of Ammonia and Convenient Ammonia Surrogates

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Abstract

Iridium-catalyzed, asymmetric allylation of ammonia as a nucleophile occurs with stereoselectivity to form a symmetric diallylamine, and related allylation of the inexpensive ammonia equivalent potassium trifluoroacetamide or the highly reactive ammonia equivalent lithium di-tert-butyliminodicarboxylate forms a range of conveniently protected, primary, α-branched allylic amines in high yields, high branched-to-linear regioselectivities, and high enantiomeric excess. The reactions of ammonia equivalents were conducted with a catalyst generated from a phosphoramidite containing a single stereochemical element.

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This article has been cited by 19 ACS Journal articles (5 most recent appear below).

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  ortho-Bromo(propa-1,2-dien-1-yl)arenes: Substrates for Domino Reactions

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  The Journal of Organic Chemistry2011 76 (21), 9060-9067

  • ortho-Bromo(propa-1,2-dien-1-yl)arenes: Substrates for Domino Reactions

    Kye-Simeon Masters, Manuela Wallesch, and Stefan Bräse
    The Journal of Organic Chemistry2011 76 (21), 9060-9067

    o-Bromo(propa-1,2-dien-1-yl)arenes exhibit novel and orthogonal reactivity under Pd catalysis in the presence of secondary amines to form enamines (concerted Pd insertion, intramolecular carbopalladation, and terminative Buchwald–Hartwig coupling) and of ...

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• 

  Oxazolidine Synthesis by Complementary Stereospecific and Stereoconvergent Methods

  Michael B. Shaghafi, Robin E. Grote, and Elizabeth R. Jarvo
  Organic Letters2011 13 (19), 5188-5191

  • Oxazolidine Synthesis by Complementary Stereospecific and Stereoconvergent Methods

    Michael B. Shaghafi, Robin E. Grote, and Elizabeth R. Jarvo
    Organic Letters2011 13 (19), 5188-5191

    Complementary stereospecific and stereoconvergent reactions for enantioselective synthesis of 1,3-oxazolidines are reported. In the presence of a rhodium catalyst, reaction of enantioenriched butadiene monoxide with aryl imines is stereospecific (99% ee). ...

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• 

  A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four α-/β- and d-/l-C-Nucleoside Stereoisomers

  Jan Štambaský, Vojtěch Kapras, Martin Štefko, Ondřej Kysilka, Michal Hocek, Andrei V. Malkov, and Pavel Kočovský
  The Journal of Organic Chemistry2011 76 (19), 7781-7803

  • A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four α-/β- and d-/l-C-Nucleoside Stereoisomers

    Jan Štambaský, Vojtěch Kapras, Martin Štefko, Ondřej Kysilka, Michal Hocek, Andrei V. Malkov, and Pavel Kočovský
    The Journal of Organic Chemistry2011 76 (19), 7781-7803

    Iridium(I)-catalyzed allylation of the enantiopure monoprotected copper(I) alkoxide, generated from (S)-5a, with the enantiopure allylic carbonates (R)-9a,b has been developed as the key step in a new approach to C-nucleoside analogues. The anomeric ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Carbon−Sulfur Bond Formation via Iridium-Catalyzed Asymmetric Allylation of Aliphatic Thiols

  Ning Gao, Shengcai Zheng, Weikang Yang, and Xiaoming Zhao
  Organic Letters2011 13 (6), 1514-1516

  • Carbon−Sulfur Bond Formation via Iridium-Catalyzed Asymmetric Allylation of Aliphatic Thiols

    Ning Gao, Shengcai Zheng, Weikang Yang, and Xiaoming Zhao
    Organic Letters2011 13 (6), 1514-1516

    An iridium-catalyzed regio- and enatioselective allylation with aliphatic thiols as the nucleophile in dichloromethane has been accomplished; and the branch products were obtained in 34−80% yields with up to 94/6 b/l and 98% ee.

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• 

  Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution

  John F. Hartwig and Levi M. Stanley
  Accounts of Chemical Research2010 43 (12), 1461-1475

  • Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution

    John F. Hartwig and Levi M. Stanley
    Accounts of Chemical Research2010 43 (12), 1461-1475

    Enantioselective allylic substitution reactions comprise some of the most versatile methods for preparing enantiomerically enriched materials. These reactions form products that contain multiple functionalities by creating carbon−nitrogen, carbon−oxygen,...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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