Literature DB >> 26138505

Dimeric TADDOL Phosphoramidites in Asymmetric Catalysis: Domino Deracemization and Cyclopropanation of Sulfonium Ylides.

Sebastian Klimczyk1, Antonio Misale1, Xueliang Huang2, Nuno Maulide3.   

Abstract

A gold-catalyzed asymmetric cyclopropanation of unactivated olefins with sulfonium ylides in the presence of a bimetallic catalyst with a novel dimeric TADDOL-phosphoramidite ligand is reported. This transformation allows a rare gold-catalyzed dynamic deracemization of chiral racemic substrates, where the same catalyst is responsible for several synergistic tasks in solution. The products are useful building blocks in synthesis and enable expeditious access to natural products.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cyclopropanation; deracemization; enantioselective synthesis; lactones; total synthesis

Year:  2015        PMID： 26138505     DOI： 10.1002/anie.201503851

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

1.  Mechanism-Guided Development of a Highly Active Bis-thiourea Catalyst for Anion-Abstraction Catalysis.

Authors:  C Rose Kennedy; Dan Lehnherr; Naomi S Rajapaksa; David D Ford; Yongho Park; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-10-11       Impact factor: 15.419

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

Review 3.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

4.  Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis.

Authors:  Jun-Qi Zhang; Yunkui Liu; Xing-Wang Wang; Liming Zhang
Journal:  Organometallics       Date:  2019-10-28       Impact factor: 3.876

Review 5.  Sulfur-Based Ylides in Transition-Metal-Catalysed Processes.

Authors:  James D Neuhaus; Rik Oost; Jérémy Merad; Nuno Maulide
Journal:  Top Curr Chem (Cham)       Date:  2018-04-13

6.  Catalyst-dependent selectivity in sulfonium ylide cycloisomerization reactions.

Authors:  Rik Oost; James D Neuhaus; Antonio Misale; Ricardo Meyrelles; Luís F Veiros; Nuno Maulide
Journal:  Chem Sci       Date:  2018-07-25       Impact factor: 9.825

7.  Direct Stereodivergent Olefination of Carbonyl Compounds with Sulfur Ylides.

Authors:  Jérémy Merad; Phillip S Grant; Tobias Stopka; Juliette Sabbatani; Ricardo Meyrelles; Alexander Preinfalk; Ján Matyasovsky; Boris Maryasin; Leticia González; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2022-06-30       Impact factor: 16.383

8.  Radical asymmetric intramolecular α-cyclopropanation of aldehydes towards bicyclo[3.1.0]hexanes containing vicinal all-carbon quaternary stereocenters.

Authors:  Liu Ye; Qiang-Shuai Gu; Yu Tian; Xiang Meng; Guo-Cong Chen; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2018-01-15       Impact factor: 14.919

9.  Gold-Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines.

Authors:  Christian Knittl-Frank; Iakovos Saridakis; Thomas Stephens; Rafael Gomes; James Neuhaus; Antonio Misale; Rik Oost; Alberto Oppedisano; Nuno Maulide
Journal:  Chemistry       Date:  2020-06-08       Impact factor: 5.020
  9 in total

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