Journal ArticleDOI
Catalytic and Enantioselective Control of the C–N Stereogenic Axis via the Pictet–Spengler Reaction
Ahreum Kim,Aram Kim,Sunjung Park,Sangji Kim,Hongil Jo,Kang Min Ok,Sang Kook Lee,Jayoung Song,Yongseok Kwon +8 more
TLDR
In this article, an unprecedented example of a chiral phosphoric acid-catalyzed atroposelective Pictet-Spengler reaction of N-arylindoles is reported.Abstract:
An unprecedented example of a chiral phosphoric acid-catalyzed atroposelective Pictet-Spengler reaction of N-arylindoles is reported. Highly enantioenriched N-aryl-tetrahydro-β-carbolines with C-N bond axial chirality are obtained via dynamic kinetic resolution. The hydrogen bond donor introduced on the bottom aromatic ring, forming a secondary interaction with the phosphoryl oxygen, is essential to achieving high enantioselectivity. A wide variety of substituents are tolerable with this transformation to provide up to 98 % ee. The application of electron-withdrawing group-substituted benzaldehydes enables the control of both axial and point stereogenicity. Biological evaluation of this new and unique scaffold shows promising antiproliferative activity and emphasizes the significance of atroposelective synthesis.read more
Citations
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Atropisomers beyond the C–C axial chirality: Advances in catalytic asymmetric synthesis
TL;DR: In this paper , a range of catalytic atroposelective approaches have been reported for the efficient synthesis of X-Y axially chiral skeletons. But, the intrinsic shorter bond length and electron-repelling effect lead to a congested hetero X−Y axis.
Journal ArticleDOI
Rational design and atroposelective synthesis of N–N axially chiral compounds
Guang-Jian Mei,Guang-Jian Mei,Jonathan J. Wong,Wenrui Zheng,Anjanay A. Nangia,Kendall N. Houk,Yixin Lu +6 more
TL;DR: The first catalytic asymmetric synthesis of N–N axially chiral compounds has been accomplished via a quinidine catalyzed N-allylic alkylation reaction via DFT calculations to understand the origin of enantioselectivity and provide guidance for the design of additional molecules of this type.
Journal ArticleDOI
Asymmetric Synthesis of Axially Chiral C−N Atropisomers
TL;DR: A review of axially chiral C−N atropisomers can be found in this paper , where a brief introduction is given to contextualize these axially Chiral skeletons, including a historical background and examples of natural products containing axially CHN axes.
Journal ArticleDOI
Catalytic Asymmetric Synthesis of Axially Chiral 3,3'‐Bisindoles by Direct Coupling of Indole Rings
TL;DR: In this article , a new enantioselective synthesis strategy for axially chiral 3,3'-bisindoles was devised by the direct coupling of two indole rings.
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Synthesis of Axially Chiral N-Arylindoles via Atroposelective Cyclization of Ynamides Catalyzed by Chiral Brønsted Acids.
TL;DR: A facile access to axially chiral N-heterocycles enabled by chiral Brønsted acid-catalyzed 5-endo-dig cyclization of ynamides is disclosed, which represents the first metal-free protocol for the construction of axiallychiral compounds from ynamide.
References
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Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates
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Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
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Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.
Daisuke Uraguchi,Masahiro Terada +1 more
TL;DR: It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines and functions as an excellent catalyst.
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Atroposelective total synthesis of axially chiral biaryl natural products.
TL;DR: Gerhard Bringmann's research interests focus on the field of analytical, synthetic, and computational natural product chemistry, i.e., on axially chiral biaryls, which is characterized by a broad structural diversity.