Literature DB >> 21359322

Enantioselective synthesis of all-carbon quaternary stereogenic centers in acyclic systems.

Jaya Prakash Das1, Ilan Marek.   

Abstract

Most of the methods for the creation of all-carbon quaternary stereogenic centers in acyclic systems were developed in the last decade showing the contemporary interest of this field of research. Initial strategies, where chiral entities were linked to carbon skeleton, to enantioselective catalysis and finally to strategies where several carbon-carbon bonds were created in a single-pot operation, reflect the constant strive and creativity in the design and execution of synthetic sequences. This feature article summarizes these sequences and is divided into sections on substitution and additions reactions, alkylation, aldol, Mannich and rearrangements reactions. It is safe to predict that this field of chemistry will continue to grow exponentially in the coming decades and the ready availability of a wide range of these chiral entities will provide an excellent opportunity to further enrich mainstream synthetic methodologies. © The Royal Society of Chemistry 2011

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Year:  2011        PMID: 21359322     DOI: 10.1039/c0cc05222a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  94 in total

1.  Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors:  Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-20       Impact factor: 15.336

2.  Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors:  Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-24       Impact factor: 15.419

3.  Merging allylic carbon-hydrogen and selective carbon-carbon bond activation.

Authors:  Ahmad Masarwa; Dorian Didier; Tamar Zabrodski; Marvin Schinkel; Lutz Ackermann; Ilan Marek
Journal:  Nature       Date:  2013-12-08       Impact factor: 49.962

4.  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

5.  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

6.  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

7.  Forming all-carbon quaternary stereogenic centres in acyclic systems from alkynes.

Authors:  Yury Minko; Morgane Pasco; Lukas Lercher; Mark Botoshansky; Ilan Marek
Journal:  Nature       Date:  2012-10-25       Impact factor: 49.962

8.  Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes.

Authors:  Takuya Hashimoto; Kazuki Sakata; Fumiko Tamakuni; Mark J Dutton; Keiji Maruoka
Journal:  Nat Chem       Date:  2013-02-10       Impact factor: 24.427

9.  Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

10.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

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