Literature DB >> 20718417

Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines.

Duy N Mai1, John P Wolfe.   

Abstract

The enantioselective synthesis of 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidine derivatives via Pd-catalyzed alkene carboamination reactions is described. These transformations generate enantiomerically enriched products with up to 94% ee from readily available alkenyl or aryl bromides and N-boc-pent-4-enylamines. The application of this method to a concise asymmetric synthesis of (-)-tylophorine is also discussed.

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Year:  2010        PMID: 20718417      PMCID: PMC2932842          DOI: 10.1021/ja106989h

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


  29 in total

1.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues.

Authors:  Myra Beaudoin Bertrand; John P Wolfe
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

3.  Discovery of 5-arylsulfonamido-3-(pyrrolidin-2-ylmethyl)-1H-indole derivatives as potent, selective 5-HT6 receptor agonists and antagonists.

Authors:  Derek C Cole; William J Lennox; Sabrina Lombardi; John W Ellingboe; Ronald C Bernotas; Gregory J Tawa; Hossein Mazandarani; Deborah L Smith; Guoming Zhang; Joseph Coupet; Lee E Schechter
Journal:  J Med Chem       Date:  2005-01-27       Impact factor: 7.446

4.  A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

5.  Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.

Authors:  Alois Fürstner; Jason W J Kennedy
Journal:  Chemistry       Date:  2006-09-25       Impact factor: 5.236

6.  Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

Authors:  Joshua E Ney; John P Wolfe
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

7.  Two-faced reactivity of alkenes: cis- versus trans-aminopalladation in aerobic Pd-catalyzed intramolecular aza-Wacker reactions.

Authors:  Guosheng Liu; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2007-04-18       Impact factor: 15.419

8.  Intramolecular aminopalladation of alkenes as a key step to pyrrolidines and related heterocycles.

Authors:  Ana Minatti; Kilian Muñiz
Journal:  Chem Soc Rev       Date:  2007-02-28       Impact factor: 54.564

9.  Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors:  Joshua E Ney; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

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

Authors:  Kai-Tai Yip; Min Yang; Ka-Lun Law; Nian-Yong Zhu; Dan Yang
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419

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  37 in total

1.  Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.

Authors:  Derick R White; Johnathon T Hutt; John P Wolfe
Journal:  J Am Chem Soc       Date:  2015-08-27       Impact factor: 15.419

2.  Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.

Authors:  Lei Miao; Imranul Haque; Maria R Manzoni; Weng Siong Tham; Sherry R Chemler
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

3.  Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Authors:  Ranjan Jana; Tejas P Pathak; Katrina H Jensen; Matthew S Sigman
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

4.  Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.

Authors:  Brett A Hopkins; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-31       Impact factor: 15.336

5.  Enantioselective Synthesis of Tetrahydroquinolines, Tetrahydroquinoxalines, and Tetrahydroisoquinolines via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  B A Hopkins; J P Wolfe
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

6.  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

7.  Recent Developments in Pd-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles.

Authors:  Danielle M Schultz; John P Wolfe
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

8.  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

9.  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

10.  Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination.

Authors:  Adam R Brown; Christopher Uyeda; Carolyn A Brotherton; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419

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