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  Chiral Brønsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH–Imine Hydrochloride Salts

Wakchaure, V. N., Obradors, C., & List, B. (2020). Chiral Brønsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH–Imine Hydrochloride Salts. Synlett, 31(17), 1707-1712. doi:10.1055/s-0040-1706413.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0007-310E-3 Version Permalink: http://hdl.handle.net/21.11116/0000-0007-310F-2
Genre: Journal Article

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 Creators:
Wakchaure, Vijay N.1, Author              
Obradors, Carla1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: Brønsted acids; N–H imine hydrochloride salt; primary amine; disulfonimide (DSI); organocatalytic reduction
 Abstract: While imines are frequently used substrates in asymmetric Brønsted acid catalysis, their corresponding salts are generally considered unsuitable reaction partners. Such processes are challenging because they require the successful competition of a catalytic amount of a chiral anion with a stoichiometric amount of an achiral one. We now show that enantiopure disulfonimides enable the asymmetric reduction of N–H imine hydrochloride salts using Hantzsch esters as hydrogen source. Our scalable reaction delivers crystalline primary amine salts in great efficiency and enantioselectivity and the discovery suggests potential of this approach in other Brønsted acid catalyzed transformations of achiral iminium salts. Kinetic studies and acidity data suggest a bifunctional catalytic activation mode.

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Language(s): eng - English
 Dates: 2020-06-192020-07-132020-08-142020-10-22
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/s-0040-1706413
 Degree: -

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Title: Synlett
  Abbreviation : Synlett
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: 31 (17) Sequence Number: - Start / End Page: 1707 - 1712 Identifier: ISSN: 0936-5214
CoNE: https://pure.mpg.de/cone/journals/resource/954925570856