Literature DB >> 22716914

Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

Shaolin Zhu1, David W C MacMillan.   

Abstract

An enantioselective arylation-cyclization cascade has been accomplished using a combination of diaryliodonium salts and asymmetric copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction of pyrroloindolines, an important alkaloid structural motif that is commonly found among biologically active natural products.

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Year:  2012        PMID： 22716914      PMCID： PMC3392034          DOI： 10.1021/ja305100g

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


  31 in total

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Journal:  J Nat Prod       Date:  2006-12       Impact factor: 4.050

2.  Antinociceptive profile of hodgkinsine.

Authors:  T A Amador; L Verotta; D S Nunes; E Elisabetsky
Journal:  Planta Med       Date:  2000-12       Impact factor: 3.352

3.  Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole.

Authors:  Pau Ruiz-Sanchis; Svetlana A Savina; Fernando Albericio; Mercedes Álvarez
Journal:  Chemistry       Date:  2011-01-12       Impact factor: 5.236

4.  Enantioselective and diastereoselective Mukaiyama-Michael reactions catalyzed by bis(oxazoline) copper(II) complexes.

Authors:  D A Evans; K A Scheidt; J N Johnston; M C Willis
Journal:  J Am Chem Soc       Date:  2001-05-16       Impact factor: 15.419

5.  Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

Authors:  Aurélien Bigot; Alice E Williamson; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2011-08-17       Impact factor: 15.419

6.  Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation.

Authors:  Bo Chen; Xue-Long Hou; Yu-Xue Li; Yun-Dong Wu
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

7.  Carbon-nitrogen bond formation involving well-defined aryl-copper(III) complexes.

Authors:  Lauren M Huffman; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

8.  Diaryliodonium salts: a journey from obscurity to fame.

Authors:  Eleanor A Merritt; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides.

Authors:  Marcin Bielawski; Berit Olofsson
Journal:  Chem Commun (Camb)       Date:  2007-03-20       Impact factor: 6.222

10.  Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions.

Authors:  Robert J Phipps; Neil P Grimster; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419
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  33 in total

1.  Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors:  Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

2.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

Review 3.  Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Authors:  Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal:  Chem Rev       Date:  2019-01-30       Impact factor: 60.622

4.  Mechanistic studies of copper(I)-catalyzed 1,3-halogen migration.

Authors:  Ryan Van Hoveln; Brandi M Hudson; Henry B Wedler; Desiree M Bates; Gabriel Le Gros; Dean J Tantillo; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2015-04-16       Impact factor: 15.419

5.  Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  European J Org Chem       Date:  2014-06-01

6.  Catalyst-controlled oligomerization for the collective synthesis of polypyrroloindoline natural products.

Authors:  Christopher R Jamison; Joseph J Badillo; Jeffrey M Lipshultz; Robert J Comito; David W C MacMillan
Journal:  Nat Chem       Date:  2017-07-24       Impact factor: 24.427

7.  Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.

Authors:  Emily C Gentry; Lydia J Rono; Martina E Hale; Rei Matsuura; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2018-02-21       Impact factor: 15.419

8.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

9.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

10.  Catalytic enantioselective cyclization and C3-fluorination of polyenes.

Authors:  Nikki A Cochrane; Ha Nguyen; Michel R Gagne
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419
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