Literature DB >> 21090654

Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Mark C Dobish1, Jeffrey N Johnston.   

Abstract

A Brønsted base-catalyzed reaction of nitroalkanes with alkyl electrophiles provides indole heterocycles substituted at C3 bearing a sec-alkyl group with good enantioselectivity (up to 90% ee). Denitration by hydrogenolysis provides a product with equally high ee. An indolenine intermediate is implicated in the addition step, and surprisingly, water cosolvent was found to have a beneficial effect in this step, leading to a one-pot protocol for elimination/enantioselective addition using PBAM, a bis(amidine) chiral nonracemic base.

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Year:  2010        PMID： 21090654      PMCID： PMC3005818          DOI： 10.1021/ol1025712

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  47 in total

1.  A Rapid Total Synthesis of Spirotryprostatin B: Proof of Its Relative and Absolute Stereochemistry F.v.N. gratefully acknowledges the Alexander-von-Humboldt-Stiftung for a Feodor-Lynen fellowship that was kindly backed by Dr. R. Breslow as second host. This research was supported by the National Institutes of Health (Grant number HL 25848). We thank Dr. H. Osada (RIKEN) for providing us with spectra of the natural product. Furthermore we are grateful to Dr. D. Lichtblau from the Nakanishi laboratory for help with the CD spectra. We acknowledge the collaborative efforts of Ms. Maria Manzoni in these studies.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-06-16       Impact factor: 15.336

2.  Total synthesis of spirotryprostatin B via asymmetric nitroolefination.

Authors:  Trusar D Bagul; Gingipalli Lakshmaiah; Takeo Kawabata; Kaoru Fuji
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

3.  New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction.

Authors:  Marco Bandini; Alfonso Melloni; Achille Umani-Ronchi
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-01       Impact factor: 15.336

4.  Total synthesis of (-)-spirotryprostatin B.

Authors:  Christiane Meyers; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-10       Impact factor: 15.336

Review 5.  Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years.

Authors:  Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

6.  Total Synthesis of (-)-Spirotryprostatin B and Three Stereoisomers We thank NIH NIGMS (GM-30859) for financial support, Prof. A. J. Shaka and N. D. Taylor for DPFGSE experiments, Prof. H. Osada for providing spectral data for natural 1, and Prof. R. M. Williams and P. R. Sebahar for providing spectral data and a sample of synthetic ent-21. We are also grateful to Prof. R. M. Williams and Prof. S. J. Danishefsky for open exchange of information prior to publication. NMR and mass spectra were determined at UC Irvine with instruments purchased with the assistance of the NSF and NIH shared instrumentation programs.

Authors:  Larry E. Overman; Mark D. Rosen
Journal:  Angew Chem Int Ed Engl       Date:  2000-12-15       Impact factor: 15.336

7.  A formal total synthesis of roseophilin: cyclopentannelation approach to the macrocyclic core.

Authors:  P E Harrington; M A Tius
Journal:  Org Lett       Date:  1999-08-26       Impact factor: 6.005

8.  Enantioselective formal total synthesis of roseophilin.

Authors:  S J Bamford; T Luker; W N Speckamp; H Hiemstra
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

9.  Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration.

Authors:  D L Boger; J Hong
Journal:  J Am Chem Soc       Date:  2001-09-05       Impact factor: 15.419

10.  Chiral proton catalysis: a catalytic enantioselective direct aza-Henry reaction.

Authors:  Benjamin M Nugent; Ryan A Yoder; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419
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  15 in total

1.  Preparation of (-)-Nutlin-3 using enantioselective organocatalysis at decagram scale.

Authors:  Tyler A Davis; Anna E Vilgelm; Ann Richmond; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2013-10-15       Impact factor: 4.354

2.  Trifluoromethylation of Secondary Nitroalkanes.

Authors:  Amber A S Gietter-Burch; Vijayarajan Devannah; Donald A Watson
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

3.  Catalytic, Enantioselective Synthesis of Stilbene cis-Diamines: A Concise Preparation of (-)-Nutlin-3, a Potent p53/MDM2 Inhibitor.

Authors:  Tyler A Davis; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2011-03-25       Impact factor: 9.825

4.  Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

5.  Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides.

Authors:  Vijayarajan Devannah; Rajgopal Sharma; Donald A Watson
Journal:  J Am Chem Soc       Date:  2019-05-17       Impact factor: 15.419

6.  Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor.

Authors:  Tyler A Davis; Michael W Danneman; Jeffrey N Johnston
Journal:  Chem Commun (Camb)       Date:  2012-04-30       Impact factor: 6.222

7.  DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.

Authors:  Thomas J Struble; Ivor Smajlagic; Hayden Foy; Travis Dudding; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2021-10-20       Impact factor: 4.354

8.  Organocatalytic, enantioselective synthesis of VNI: a robust therapeutic development platform for Chagas, a neglected tropical disease.

Authors:  Mark C Dobish; Fernando Villalta; Michael R Waterman; Galina I Lepesheva; Jeffrey N Johnston
Journal:  Org Lett       Date:  2012-12-07       Impact factor: 6.005

9.  Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid-Base Catalyst with Recycle.

Authors:  Sergey V Tsukanov; Martin D Johnson; Scott A May; Morgan Rosemeyer; Michael A Watkins; Stanley P Kolis; Matthew H Yates; Jeffrey N Johnston
Journal:  Org Process Res Dev       Date:  2016-02-01       Impact factor: 3.317

10.  Preparation of H,(4) PyrrolidineQuin-BAM (PBAM).

Authors:  Tyler A Davis; Mark C Dobish; Kenneth E Schwieter; Aspen C Chun; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2012-02-22
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