Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaSNAr

Mariel M. Cardenas; Mirza A. Saputra; Deane A. Gordon; Andrea N. Sanchez; Nobuyuki Yamamoto; Jeffrey L. Gustafson

doi:10.1039/d1cc04335h

Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaS_NAr

Mariel M. Cardenas, Mirza A. Saputra, Deane A. Gordon, Andrea N. Sanchez, Nobuyuki Yamamoto, Jeffrey L. Gustafson

Faculty of Advanced Technology and Multidiscipline

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolinesviathe nucleophilic aromatic substitution (S_NAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceededviaDKR while higher barrier substrates proceededviaKR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.

Original language	English
Pages (from-to)	10087-10090
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	78
DOIs	https://doi.org/10.1039/d1cc04335h
Publication status	Published - 7 Oct 2021

Access to Document

10.1039/d1cc04335h

Cite this

@article{d5b1a8d77b1f4c438c331eca44c2abeb,

title = "Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaSNAr",

abstract = "Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolinesviathe nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceededviaDKR while higher barrier substrates proceededviaKR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.",

author = "Cardenas, {Mariel M.} and Saputra, {Mirza A.} and Gordon, {Deane A.} and Sanchez, {Andrea N.} and Nobuyuki Yamamoto and Gustafson, {Jeffrey L.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = oct,

day = "7",

doi = "10.1039/d1cc04335h",

language = "English",

volume = "57",

pages = "10087--10090",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "78",

}

TY - JOUR

T1 - Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaSNAr

AU - Cardenas, Mariel M.

AU - Saputra, Mirza A.

AU - Gordon, Deane A.

AU - Sanchez, Andrea N.

AU - Yamamoto, Nobuyuki

AU - Gustafson, Jeffrey L.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/10/7

Y1 - 2021/10/7

N2 - Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolinesviathe nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceededviaDKR while higher barrier substrates proceededviaKR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.

AB - Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolinesviathe nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceededviaDKR while higher barrier substrates proceededviaKR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.

UR - http://www.scopus.com/inward/record.url?scp=85116194761&partnerID=8YFLogxK

U2 - 10.1039/d1cc04335h

DO - 10.1039/d1cc04335h

M3 - Article

C2 - 34515276

AN - SCOPUS:85116194761

SN - 1359-7345

VL - 57

SP - 10087

EP - 10090

JO - Chemical Communications

JF - Chemical Communications

IS - 78

ER -

Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaSNAr

Abstract

Access to Document

Fingerprint

Cite this

Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaS_NAr