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Literature DB >> 15067132

Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines.

Chunmei Wei¹, Joel T Mague, Chao-Jun Li.

Abstract

A Cu(I)-catalyzed direct addition of alkynes to imines was developed. The process is simple and provides a diverse range of propargylamines in high enantiomeric excess and good yield both in water and in toluene. The absolute configuration of such addition products has been determined by x-ray crystallography.

Entities: Chemical

Year: 2004 PMID： 15067132 PMCID： PMC395979 DOI： 10.1073/pnas.0307150101

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

24 in total

1. Additions of Organometallic Reagents to C=N Bonds: Reactivity and Selectivity.

Authors: Robert Bloch
Journal: Chem Rev Date: 1998-06-18 Impact factor: 60.622

2. A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes.

Authors: N K Anand; E M Carreira
Journal: J Am Chem Soc Date: 2001-10-03 Impact factor: 15.419

3. Titanocene-catalyzed regioselective syn-hydrosilation of alkynes.

Authors: Tamotsu Takahashi; Fengyu Bao; Guohua Gao; Masamichi Ogasawara
Journal: Org Lett Date: 2003-09-18 Impact factor: 6.005

4. Enantioselective synthesis of propargylamines by copper-catalyzed addition of alkynes to enamines.

Authors: Christopher Koradin; Kurt Polborn; Paul Knochel
Journal: Angew Chem Int Ed Engl Date: 2002-07-15 Impact factor: 15.336

5. Tandem Cyclization of Alkynylmetals Bearing a Remote Leaving Group via Cycloalkylidene Carbenes.

Authors:
Journal: Org Lett Date: 2000-06-29 Impact factor: 6.005

Review 6. The discovery of novel reactivity in the development of C-C bond-forming reactions: in situ generation of zinc acetylides with Zn(II)/R(3)N.

Authors: D E Frantz; R Fassler; C S Tomooka; E M Carreira
Journal: Acc Chem Res Date: 2000-06 Impact factor: 22.384

7. Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene.

Authors: Chunmei Wei; Chao-Jun Li
Journal: J Am Chem Soc Date: 2002-05-22 Impact factor: 15.419

8. Highly efficient Grignard-type imine additions via C-H activation in water and under solvent-free conditions.

Authors: Chao-Jun Li; Chunmei Wei
Journal: Chem Commun (Camb) Date: 2002-02-07 Impact factor: 6.222

9. Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines.

Authors: Laura C Akullian; Marc L Snapper; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2003-09-15 Impact factor: 15.336

10. Catalytic, three-component assembly reaction for the synthesis of pyrrolidines.

Authors: Chris V Galliford; Melissa A Beenen; SonBinh T Nguyen; Karl A Scheidt
Journal: Org Lett Date: 2003-09-18 Impact factor: 6.005

9 in total

1. Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.

Authors: Zhiping Li; D Scott Bohle; Chao-Jun Li
Journal: Proc Natl Acad Sci U S A Date: 2006-06-05 Impact factor: 11.205

2. Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

Authors: Anh T Tran; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-07-24 Impact factor: 15.336

3. The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors: Barry M Trost; Andrew H Weiss
Journal: Adv Synth Catal Date: 2009-05 Impact factor: 5.837

4. Silver(I) triflate-catalyzed direct synthesis of N-PMP protected alpha-aminopropargylphosphonates from terminal alkynes.

Authors: Rajasekhar Dodda; Cong-Gui Zhao
Journal: Org Lett Date: 2007-01-04 Impact factor: 6.005