Literature DB >> 34060818

Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of syn-sec,tert-Diols via (Z)-σ-Allylmetal Intermediates.

Ming Xiang1, Dana E Pfaffinger1, Eliezer Ortiz1, Gilmar A Brito1, Michael J Krische1.   

Abstract

The first catalytic enantioselective ruthenium-catalyzed carbonyl reductive couplings of allene pronucleophiles is described. Using an iodide-modified ruthenium-BINAP-catalyst and O-benzhydryl alkoxyallene 1a, carbonyl (α-alkoxy)allylation occurs from the alcohol or aldehyde oxidation level to form enantiomerically enriched syn-sec,tert-diols. Internal chelation directs intervention of (Z)-σ-alkoxyallylruthenium isomers, which engage in stereospecific carbonyl addition.

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Year:  2021        PMID： 34060818      PMCID： PMC8299538          DOI： 10.1021/jacs.1c03480

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   16.383


  32 in total

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Authors:  Pier Paolo Giovannini; Giancarlo Fantin; Alessandro Massi; Valentina Venturi; Paola Pedrini
Journal:  Org Biomol Chem       Date:  2011-10-18       Impact factor: 3.876

Review 2.  Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.

Authors:  Khoa D Nguyen; Boyoung Y Park; Tom Luong; Hiroki Sato; Victoria J Garza; Michael J Krische
Journal:  Science       Date:  2016-10-21       Impact factor: 47.728

3.  Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C-N, C-C, and C-O Bonds.

Authors:  Rémi Blieck; Marc Taillefer; Florian Monnier
Journal:  Chem Rev       Date:  2020-12-10       Impact factor: 60.622

4.  Blockage of the early step of lankacidin biosynthesis caused a large production of pentamycin, citreodiol and epi-citreodiol in Streptomyces rochei.

Authors:  Zhisheng Cao; Ryuhei Yoshida; Haruyasu Kinashi; Kenji Arakawa
Journal:  J Antibiot (Tokyo)       Date:  2014-12-03       Impact factor: 2.649

5.  Iodide effects in transition metal catalyzed reactions.

Authors:  Peter M Maitlis; Anthony Haynes; Brian R James; Marta Catellani; Gian Paolo Chiusoli
Journal:  Dalton Trans       Date:  2004-09-20       Impact factor: 4.390

6.  Ruthenium- and palladium-catalyzed enyne cycloisomerizations: differentially stereoselective syntheses of bicyclic structures.

Authors:  Barry M Trost; Eric M Ferreira; Alicia C Gutierrez
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

7.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

8.  Silyl-substituted spirodiepoxides: stereoselective formation and regioselective opening.

Authors:  Partha Ghosh; Joseph R Cusick; Jennifer Inghrim; Lawrence J Williams
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

Review 9.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

Review 10.  Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates.

Authors:  Alexander P Pulis; Kay Yeung; David J Procter
Journal:  Chem Sci       Date:  2017-06-08       Impact factor: 9.825
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  3 in total

1.  Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl-Cu Species.

Authors:  Yuyang Dong; Alexander W Schuppe; Binh Khanh Mai; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2022-03-26       Impact factor: 16.383

2.  Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic syn- or anti-1,2-Diols from Aldehydes and Dienol Ethers.

Authors:  Thomas Q Davies; John J Murphy; Maxime Dousset; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2021-08-19       Impact factor: 15.419

Review 3.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020
  3 in total

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