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Literature DB >> 27531137

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

Abstract

The first Ir-catalyzed enantioselective allylation of trisubstituted allylic electrophiles has been developed. Through modification of the leaving group of allylic electrophiles, we found that trisubstituted allylic phosphates are suitable electrophiles for asymmetric allylation. The reaction of allylic phosphates with enol silanes derived from dioxinones gave allylated products in good yields with high enantioselectivities.

Entities: Chemical

Keywords: 1,1′-substituted olefins; allylic asymmetric substitution; allylic phosphates; dioxinones; iridium catalysis

Mesh：

Substances：

Year: 2016 PMID： 27531137 PMCID： PMC5213737 DOI： 10.1002/anie.201607053

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

54 in total

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

Authors: Takatoshi Kanayama; Kazumasa Yoshida; Hideto Miyabe; Yoshiji Takemoto
Journal: Angew Chem Int Ed Engl Date: 2003-05-09 Impact factor: 15.336

2. Enantioselective synthesis of spiro cyclopentane-1,3'-indoles and 2,3,4,9-tetrahydro-1H-carbazoles by iridium-catalyzed allylic dearomatization and stereospecific migration.

Authors: Qing-Feng Wu; Chao Zheng; Shu-Li You
Journal: Angew Chem Int Ed Engl Date: 2012-01-05 Impact factor: 15.336

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

Authors: Wen-Bo Liu; Chao Zheng; Chun-Xiang Zhuo; Li-Xin Dai; Shu-Li You
Journal: J Am Chem Soc Date: 2012-02-24 Impact factor: 15.419

4. Iridium-catalyzed intramolecular asymmetric allylic dearomatization of phenols.

Authors: Qing-Feng Wu; Wen-Bo Liu; Chun-Xiang Zhuo; Zi-Qiang Rong; Ke-Yin Ye; Shu-Li You
Journal: Angew Chem Int Ed Engl Date: 2011-04-07 Impact factor: 15.336

5. Iridium-catalyzed enantioselective allyl-allylsilane cross-coupling.

Authors: James Y Hamilton; Nicole Hauser; David Sarlah; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2014-08-11 Impact factor: 15.336

6. 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

7. 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

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. Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α-Alkoxy Ketones.

Authors: Xingyu Jiang; Wenyong Chen; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2016-04-01 Impact factor: 15.336

10. A broadly applicable NHC-Cu-catalyzed approach for efficient, site-, and enantioselective coupling of readily accessible (pinacolato)alkenylboron compounds to allylic phosphates and applications to natural product synthesis.

Authors: Fang Gao; James L Carr; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2014-01-28 Impact factor: 15.419

3 in total

1. Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis.

Authors: Xingyu Jiang; Philip Boehm; John F Hartwig
Journal: J Am Chem Soc Date: 2018-01-17 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. Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

Authors: Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2017-08-09 Impact factor: 15.336

3 in total