Literature DB >> 25223593

Iridium-catalyzed regio- and enantioselective allylic substitution of silyl dienolates derived from dioxinones.

Ming Chen1, John F Hartwig.   

Abstract

Reported herein is the iridium-catalyzed regio- and enantioselective allylic substitution reactions of unstabilized silyl dienolates derived from dioxinones. Asymmetric allylic substitution of a variety of allylic trichloroethyl carbonates with these silyl dienolates gave γ-allylated products selectively in 60-84% yield and 90-98% ee.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkylation; allylic compounds; asymmetric catalysis; enantioselectivity; iridium

Mesh：

Substances：

Year:  2014        PMID： 25223593      PMCID： PMC4214550          DOI： 10.1002/anie.201406778

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


  39 in total

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2.  Enantio- and diastereoselective ir-catalyzed allylic substitutions for asymmetric synthesis of amino acid derivatives.

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

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4.  Iridium-catalyzed allylic alkylation reaction with N-aryl phosphoramidite ligands: scope and mechanistic studies.

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Journal:  J Am Chem Soc       Date:  2012-02-24       Impact factor: 15.419

5.  Organocatalytic Highly enantioselective alpha-arylation of beta-ketoesters.

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6.  Enantioselective arylation of 2-methylacetoacetates catalyzed by CuI/trans-4-hydroxy-L-proline at low reaction temperatures.

Authors:  Xiaoan Xie; Yu Chen; Dawei Ma
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

7.  Iridium-catalyzed enantioselective allyl-alkene coupling.

Authors:  James Y Hamilton; David Sarlah; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2014-02-12       Impact factor: 15.419

8.  Total synthesis and structural revision of the marine macrolide neopeltolide.

Authors:  Daniel W Custar; Thomas P Zabawa; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

9.  Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion.

Authors:  Wenyong Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-01-30       Impact factor: 15.419

10.  Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps.

Authors:  Michael Palucki; Joann M Um; Nobuyoshi Yasuda; David A Conlon; Fuh-Rong Tsay; Frederick W Hartner; Yi Hsiao; Benjamin Marcune; Sandor Karady; David L Hughes; Peter G Dormer; Paul J Reider
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354
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  8 in total

1.  Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement.

Authors:  Wen-Bo Liu; Noriko Okamoto; Eric J Alexy; Allen Y Hong; Kristy Tran; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-04-18       Impact factor: 15.419

2.  Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.

Authors:  Xingyu Jiang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

3.  Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-17       Impact factor: 15.336

4.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

5.  Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.

Authors:  Jacqueline Bitai; Alastair J Nimmo; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-28       Impact factor: 16.823

6.  A Desilylative Approach to Alkyl Substituted C(1)-Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions.

Authors:  Yihong Wang; Claire M Young; Honglei Liu; Will C Hartley; Max Wienhold; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

7.  Topochemical, Single-Crystal-to-Single-Crystal [2+2] Photocycloadditions Driven by Chalcogen-Bonding Interactions.

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8.  Catalytic Activation of Imines by Chalcogen Bond Donors in a Povarov [4+2] Cycloaddition Reaction.

Authors:  Tim Steinke; Patrick Wonner; Richard M Gauld; Sascha Heinrich; Stefan M Huber
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  8 in total

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