NDLI: Pd(II)-Catalyzed Enantioselective C(sp<sup>3</sup>)-H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines.

Please wait, while we are loading the content...

Pd(II)-Catalyzed Enantioselective C(sp³)-H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines.

Content Provider	Europe PMC
Author	Rodrigalvarez, Jesus Reeve, Luke A. Miró, Javier Gaunt, Matthew J.
Copyright Year	2022
Abstract	Strained aminomethyl-cycloalkanesare a recurrent scaffold in medicinalchemistry due to their unique structural features that give rise toa range of biological properties. Here, we report a palladium-catalyzedenantioselective C(sp3)–H arylation of aminomethyl-cyclopropanesand -cyclobutanes with aryl boronic acids. A range of native tertiaryalkylamine groups are able to direct C–H cleavage and forgecarbon-aryl bonds on the strained cycloalkanes framework as singlediastereomers and with excellent enantiomeric ratios. Central to thesuccess of this strategy is the use of a simple N-acetyl amino acid ligand, which not only controls the enantioselectivitybut also promotes γ-C–H activation of over other pathways.Computational analysis of the cyclopalladation step provides an understandingof how enantioselective C–H cleavage occurs and revealed distincttransition structures to our previous work on enantioselective desymmetrizationof N-isobutyl tertiary alkylamines. This straightforwardand operationally simple method simplifies the construction of functionalizedaminomethyl-strained cycloalkanes, which we believe will find widespreaduse in academic and industrial settings relating to the synthesisof biologically active small molecules.
ISSN	00027863
Volume Number	144
PubMed Central reference number	PMC9097487
Issue Number	9
PubMed reference number	35212219
Journal	Journal of the American Chemical Society [J. Am. Chem. Soc]
e-ISSN	15205126
DOI	10.1021/jacs.1c11921
Language	English
Publisher	American Chemical Society
Publisher Date	2022-02-25
Access Restriction	Open
Rights License	Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). © 2022 American Chemical Society
Content Type	Text
Resource Type	Article
Subject	Chemistry Colloid and Surface Chemistry Biochemistry Catalysis

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines.

Pd(II)-Catalyzed Enantioselective C(sp³)-H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines.