Literature DB >> 14724294

Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Christopher J Douglas1, Larry E Overman.   

Abstract

Only a few catalytic asymmetric C-C bond-forming reactions have been shown to be useful for constructing all-carbon quaternary stereocenters. This Perspective examines the current state of such methods.

Entities:  

Year:  2004        PMID： 14724294      PMCID： PMC397386          DOI： 10.1073/pnas.0307113101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  27 in total

1.  Enantioselective Organocatalysis.

Authors:  Peter I. Dalko; Lionel Moisan
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-15       Impact factor: 15.336

2.  Modular Pyridinyl Peptide Ligands in Asymmetric Catalysis: Enantioselective Synthesis of Quaternary Carbon Atoms Through Copper-Catalyzed Allylic Substitutions This research was supported by the National Institutes of Health (GM47480 and GM57212). Additional funds were provided by DuPont.

Authors:  Courtney A. Luchaco-Cullis; Hirotake Mizutani; Kerry E. Murphy; Amir H. Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-17       Impact factor: 15.336

3.  Enantioselective Construction of Quaternary Stereocenters.

Authors:  Jens Christoffers; Alexander Mann
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

4.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

5.  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

6.  Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile.

Authors:  Ara H Mermerian; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-04-09       Impact factor: 15.419

7.  Highly Enantioselective Palladium-Catalyzed Ene-Type Cyclization of a 1,6-Enyne We are grateful to Drs. H. Kumobayashi, T. Miura, and N. Sayo of Takasago International Co. for providing the BINAP and SEGPHOS ligands. We also thank Dr. M. Yamasaki and Mr. S. Sato of RIGAKU Co. for the X-ray analyses.

Authors:  Manabu Hatano; Masahiro Terada; Koichi Mikami
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

8.  Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones.

Authors:  Dirk J Spielvogel; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-04-10       Impact factor: 15.419

9.  Enantioselective Staudinger synthesis of beta-lactams catalyzed by a planar-chiral nucleophile.

Authors:  Brian L Hodous; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

10.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419
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  111 in total

1.  Total synthesis of asperazine.

Authors:  S P Govek; L E Overman
Journal:  J Am Chem Soc       Date:  2001-09-26       Impact factor: 15.419

2.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

3.  High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates.

Authors:  Nolan T McDougal; Scott C Virgil; Brian M Stoltz
Journal:  Synlett       Date:  2010-01-01       Impact factor: 2.454

4.  An organocatalytic asymmetric Nazarov cyclization.

Authors:  Ashok K Basak; Naoyuki Shimada; William F Bow; David A Vicic; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

5.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

6.  Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-09       Impact factor: 15.336

7.  Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2017-07-05       Impact factor: 2.415

8.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

9.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04

10.  Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419
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