Literature DB >> 15387540

Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation.

Alexandre Alexakis1, Damien Polet.   

Abstract

[reaction: see text] Linear or branched allylic carbonates or acetates undergo enantioselective iridium-catalyzed allylic substitution with sodium malonate. The reaction is wide in scope and affords the branched product in high yield and with high regio- (up to >99:1) and enantioselectivity (up to 98%). Ten aromatic or aliphatic substrates were successfully tested.

Entities:  

Year:  2004        PMID： 15387540     DOI： 10.1021/ol048607y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors:  John F Hartwig; Levi M Stanley
Journal:  Acc Chem Res       Date:  2010-09-28       Impact factor: 22.384

2.  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

3.  Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-28       Impact factor: 15.336

4.  Total synthesis of enantiopure (+)-gamma-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation.

Authors:  Bruno D Chapsal; Iwao Ojima
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

5.  Construction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis.

Authors:  Wen-Bo Liu; Corey M Reeves; Scott C Virgil; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-07-12       Impact factor: 15.419

6.  Iridium-catalyzed kinetic asymmetric transformations of racemic allylic benzoates.

Authors:  Levi M Stanley; Chen Bai; Mitsuhiro Ueda; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

7.  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

8.  The allyl intermediate in regioselective and enantioselective iridium-catalyzed asymmetric allylic substitution reactions.

Authors:  Sherzod T Madrahimov; Dean Markovic; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419

9.  Enantio-, diastereo-, and regioselective iridium-catalyzed asymmetric allylic alkylation of acyclic β-ketoesters.

Authors:  Wen-Bo Liu; Corey M Reeves; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419

10.  Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Synlett       Date:  2018-08-15       Impact factor: 2.454
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