Literature DB >> 17302421

Cation-pi control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams.

Lei Yao1, Jeffrey Aubé.   

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Year:  2007        PMID： 17302421      PMCID： PMC2596723          DOI： 10.1021/ja068919r

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


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  12 in total

1.  Regiocontrol in an intramolecular Schmidt reaction: total synthesis of (+)-aspidospermidine.

Authors:  R Iyengar; K Schildknegt; J Aubé
Journal:  Org Lett       Date:  2000-06-01       Impact factor: 6.005

2.  The Cationminus signpi Interaction.

Authors:  Jennifer C. Ma; Dennis A. Dougherty
Journal:  Chem Rev       Date:  1997-08-05       Impact factor: 60.622

3.  Cation-pi interactions as a tool to enhance the power of a chiral auxiliary during asymmetric photoreactions within zeolites.

Authors:  Lakshmi S Kaanumalle; J Sivaguru; N Arunkumar; S Karthikeyan; V Ramamurthy
Journal:  Chem Commun (Camb)       Date:  2003-01-07       Impact factor: 6.222

4.  A combined intramolecular Diels-Alder/intramolecular schmidt reaction: formal synthesis of (+/-)-stenine.

Authors:  Jennifer E Golden; Jeffrey Aubé
Journal:  Angew Chem Int Ed Engl       Date:  2002-11-15       Impact factor: 15.336

5.  Facile C-N cleavage in a series of bridged lactams.

Authors:  Yao Lei; Aaron D Wrobleski; Jennifer E Golden; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

6.  Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate.

Authors:  Kousuke Tani; Brian M Stoltz
Journal:  Nature       Date:  2006-06-08       Impact factor: 49.962

7.  Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.

Authors:  Rajesh Iyengar; Klaas Schildknegt; Martha Morton; Jeffrey Aubé
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

8.  Face-selective addition to a cation-pi complex of a pyridinium salt: synthesis of chiral 1,4-dihydropyridines.

Authors:  Shinji Yamada; Chisako Morita
Journal:  J Am Chem Soc       Date:  2002-07-17       Impact factor: 15.419

9.  Twisted amide reduction under Wolff-Kishner conditions: synthesis of a benzo-1-aza-adamantane derivative.

Authors:  Crystal G Bashore; Ivan J Samardjiev; Jon Bordner; Jotham W Coe
Journal:  J Am Chem Soc       Date:  2003-03-19       Impact factor: 15.419

10.  Unusual tethering effects in the Schmidt reaction of hydroxyalkyl azides with ketones: cation-pi and steric stabilization of a pseudoaxial phenyl group.

Authors:  Christopher E Katz; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2003-11-19       Impact factor: 15.419
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  17 in total

1.  Structural characterization of N-protonated amides: regioselective N-activation of medium-bridged twisted lactams.

Authors:  Michal Szostak; Lei Yao; Victor W Day; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

2.  Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex.

Authors:  Marc Liniger; David G VanderVelde; Michael K Takase; Mona Shahgholi; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-01-12       Impact factor: 15.419

3.  The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization.

Authors:  Sirilata Yotphan; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-02-05       Impact factor: 15.419

Review 4.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

Review 5.  The Cation-π Interaction in Small-Molecule Catalysis.

Authors:  C Rose Kennedy; Song Lin; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-22       Impact factor: 15.336

6.  Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.

Authors:  Beau P Pritchett; Etienne J Donckele; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-05       Impact factor: 15.336

7.  Corey-Chaykovsky epoxidation of twisted amides: synthesis and reactivity of bridged spiro-epoxyamines.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

8.  Direct synthesis of medium-bridged twisted amides via a transannular cyclization strategy.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

9.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

10.  Proximity effects in nucleophilic addition reactions to medium-bridged twisted lactams: remarkably stable tetrahedral intermediates.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
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