Literature DB >> 16522078

Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

Kai-Tai Yip1, Min Yang, Ka-Lun Law, Nian-Yong Zhu, Dan Yang.   

Abstract

We have developed an efficient Pd(II)-catalyzed enantioselective oxidative tandem cyclization strategy using molecular oxygen as a green oxidant for the double 5-exo-trig cyclizations of N-(2-allylaryl) amides to afford a variety of indolines in good yields without the formation of undesired monocyclization products. By employing Pd(TFA)2/(-)-sparteine as the chiral catalyst, we obtained tandem cyclization products with high enantioselectivity (up to 91% ee).

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Year:  2006        PMID： 16522078     DOI： 10.1021/ja060291x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  40 in total

1.  Kinetic resolutions of indolines by a nonenzymatic acylation catalyst.

Authors:  Forrest O Arp; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-11-08       Impact factor: 15.419

2.  The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

Authors:  Sherry R Chemler
Journal:  Org Biomol Chem       Date:  2009       Impact factor: 3.876

3.  Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

4.  Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid.

Authors:  Erik C Carlson; Lauren K Rathbone; Hua Yang; Nathan D Collett; Rich G Carter
Journal:  J Org Chem       Date:  2008-06-05       Impact factor: 4.354

5.  Synthesis of acyclic alpha,beta-unsaturated ketones via Pd(II)-catalyzed intermolecular reaction of alkynamides and alkenes.

Authors:  Norie Momiyama; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-02-06       Impact factor: 15.419

6.  Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants.

Authors:  Vincent Escande; Brice-Loïc Renard; Claude Grison
Journal:  Environ Sci Pollut Res Int       Date:  2014-09-30       Impact factor: 4.223

7.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

8.  3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

Authors:  Emilia J Groso; Alexander N Golonka; Ryan A Harding; Brandon W Alexander; Taylor M Sodano; Corinna S Schindler
Journal:  ACS Catal       Date:  2018-01-18       Impact factor: 13.084

9.  Reconciling the stereochemical course of nucleopalladation with the development of enantioselective wacker-type cyclizations.

Authors:  Adam B Weinstein; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

10.  Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

Authors:  Xuan Ye; Paul B White; Shannon S Stahl
Journal:  J Org Chem       Date:  2012-11-30       Impact factor: 4.354
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