Literature DB >> 26235369

Diastereo- and Enantioselective Iridium Catalyzed Carbonyl (α-Cyclopropyl)allylation via Transfer Hydrogenation.

Ryosuke Tsutsumi1, Suckchang Hong1, Michael J Krische2.   

Abstract

The first examples of diastereo- and enantioselective carbonyl α-(cyclopropyl)allylation are reported. Under the conditions of iridium catalyzed transfer hydrogenation using the chiral precatalyst (R)-Ir-I modified by SEGPHOS, carbonyl α-(cyclopropyl)allylation may be achieved with equal facility from alcohol or aldehyde oxidation levels. This methodology provides a conduit to hitherto inaccessible inaccessible enantiomerically enriched cyclopropane-containing architectures.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cyclopropane; enantioselective catalysis; green chemistry; iridium; transfer hydrogenation

Mesh：

Substances：

Year:  2015        PMID： 26235369      PMCID： PMC4627847          DOI： 10.1002/chem.201502499

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  32 in total

Review 1.  Biosynthesis and metabolism of cyclopropane rings in natural compounds.

Authors:  Ludger A Wessjohann; Wolfgang Brandt; Thies Thiemann
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Creation of quaternary stereocenters in carbonyl allylation reactions.

Authors:  Ilan Marek; Genia Sklute
Journal:  Chem Commun (Camb)       Date:  2006-12-06       Impact factor: 6.222

3.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

Review 4.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
Journal:  Chem Soc Rev       Date:  2009-07-10       Impact factor: 54.564

Review 5.  New and unusual scaffolds in medicinal chemistry.

Authors:  Charles M Marson
Journal:  Chem Soc Rev       Date:  2011-08-12       Impact factor: 54.564

6.  Catalytic enantioselective allylation of carbonyl compounds and imines.

Authors:  Miguel Yus; José C González-Gómez; Francisco Foubelo
Journal:  Chem Rev       Date:  2011-09-16       Impact factor: 60.622

7.  Cooperative titanocene and phosphine catalysis: accelerated C-X activation for the generation of reactive organometallics.

Authors:  Lauren M Fleury; Andrew D Kosal; James T Masters; Brandon L Ashfeld
Journal:  J Org Chem       Date:  2012-12-31       Impact factor: 4.354

8.  Carbocycles from donor-acceptor cyclopropanes.

Authors:  Huck K Grover; Michael R Emmett; Michael A Kerr
Journal:  Org Biomol Chem       Date:  2015-01-21       Impact factor: 3.876

9.  Iridium catalyzed carbocyclizations: efficient (5+2) cycloadditions of vinylcyclopropanes and alkynes.

Authors:  Michaela-Christina Melcher; Henrik von Wachenfeldt; Anders Sundin; Daniel Strand
Journal:  Chemistry       Date:  2014-11-20       Impact factor: 5.236

10.  Vinylcyclopropane derivatives in transition-metal-catalyzed cycloadditions for the synthesis of carbocyclic compounds.

Authors:  Lei Jiao; Zhi-Xiang Yu
Journal:  J Org Chem       Date:  2013-06-25       Impact factor: 4.354
View more
  4 in total

1.  Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes.

Authors:  James M Cabrera; Johannes Tauber; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-04       Impact factor: 15.336

2.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384

3.  An Expeditious Synthesis of Sialic Acid Derivatives by Copper(I)-Catalyzed Stereodivergent Propargylation of Unprotected Aldoses.

Authors:  Xiao-Feng Wei; Yohei Shimizu; Motomu Kanai
Journal:  ACS Cent Sci       Date:  2016-01-04       Impact factor: 14.553

4.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.