Literature DB >> 34323490

α,α'-C-H Bond Difunctionalization of Unprotected Alicyclic Amines.

Daniel A Valles1, Subhradeep Dutta1, Anirudra Paul1, Khalil A Abboud2, Ion Ghiviriga3, Daniel Seidel1.   

Abstract

A simple one-pot procedure enables the sequential, regioselective, and diastereoselective introduction of the same or two different substituents to the α- and α'-positions of unprotected azacycles. Aryl, alkyl, and alkenyl substituents are introduced via their corresponding organolithium compounds. The scope of this transformation includes pyrrolidines, piperidines, azepanes, and piperazines.

Entities:  

Year:  2021        PMID： 34323490      PMCID： PMC8609614          DOI： 10.1021/acs.orglett.1c02187

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.072


  63 in total

1.  Intramolecular redox-triggered C-H functionalization.

Authors:  Igor D Jurberg; Bo Peng; Eckhard Wöstefeld; Maximilian Wasserloos; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-19       Impact factor: 15.336

2.  Ru(3)(CO)(12)-catalyzed coupling reaction of sp(3) C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes.

Authors:  N Chatani; T Asaumi; S Yorimitsu; T Ikeda; F Kakiuchi; S Murai
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

3.  Zirconium Catalyzed Hydroaminoalkylation for the Synthesis of α-Arylated Amines and N-Heterocycles.

Authors:  Ana Koperniku; Laurel L Schafer
Journal:  Chemistry       Date:  2021-03-04       Impact factor: 5.236

4.  Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3 and a Chiral Lewis Acid Co-Catalyst.

Authors:  Yejin Chang; Min Cao; Jessica Z Chan; Cunyuan Zhao; Yuankai Wang; Rose Yang; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2021-01-29       Impact factor: 15.419

5.  Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes.

Authors:  Shyam Basak; Laura Winfrey; Betty A Kustiana; Rebecca L Melen; Louis C Morrill; Alexander P Pulis
Journal:  Chem Soc Rev       Date:  2021-02-03       Impact factor: 54.564

6.  Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.

Authors:  Morgan M Walker; Brian Koronkiewicz; Shuming Chen; K N Houk; James M Mayer; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

7.  New Strategies for the Transition-Metal Catalyzed Synthesis of Aliphatic Amines.

Authors:  Aaron Trowbridge; Scarlett M Walton; Matthew J Gaunt
Journal:  Chem Rev       Date:  2020-02-17       Impact factor: 60.622

8.  α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Authors:  Jillian E Spangler; Yoshihisa Kobayashi; Pritha Verma; Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-09-10       Impact factor: 15.419

9.  Classical-Reaction-Driven Stereo- and Regioselective C(sp(3) )-H Functionalization of Aliphatic Amines.

Authors:  Sujit Mahato; Chandan K Jana
Journal:  Chem Rec       Date:  2016-05-17       Impact factor: 6.771

10.  C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.

Authors:  Ming Shang; Jessica Z Chan; Min Cao; Yejin Chang; Qifan Wang; Brennan Cook; Sebastian Torker; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2018-08-10       Impact factor: 15.419
View more
  2 in total

1.  Regioselective α-Cyanation of Unprotected Alicyclic Amines.

Authors:  Fuchao Yu; Daniel A Valles; Weijie Chen; Scott D Daniel; Ion Ghiviriga; Daniel Seidel
Journal:  Org Lett       Date:  2022-08-29       Impact factor: 6.072

2.  Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.

Authors:  Anirudra Paul; Camille Vasseur; Scott D Daniel; Daniel Seidel
Journal:  Org Lett       Date:  2022-01-31       Impact factor: 6.072
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.