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Literature DB >> 19954200

Iridium-catalyzed, regio- and enantioselective allylic substitution with aromatic and aliphatic sulfinates.

Abstract

The iridium-catalyzed allylation of sodium sulfinate to form branched allylic sulfones is reported. The reactions between various sodium sulfinates and achiral allylic carbonates occur in good yields, with high selectivity for the branched isomer, and high enantioselectivities (up to 98% ee).

Entities: Chemical

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Year: 2010 PMID： 19954200 PMCID： PMC2802463 DOI： 10.1021/ol9023248

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

28 in total

1. Regio- and enantioselective allylic amination of achiral allylic esters catalyzed by an iridium-phosphoramidite complex.

Authors: Toshimichi Ohmura; John F Hartwig
Journal: J Am Chem Soc Date: 2002-12-25 Impact factor: 15.419

2. Synthesis of trisubstituted alkenes via olefin cross-metathesis.

Authors: A K Chatterjee; R H Grubbs
Journal: Org Lett Date: 1999-12-02 Impact factor: 6.005

3. Pd-catalyzed enantioselective allylic substitution: new strategic options for the total synthesis of natural products.

Authors: Timm Graening; Hans-Günther Schmalz
Journal: Angew Chem Int Ed Engl Date: 2003-06-16 Impact factor: 15.336

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

Authors: Barry M Trost; Matthew L Crawley
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

5. Practical Pd/C-mediated allylic substitution in water.

Authors: François-Xavier Felpin; Yannick Landais
Journal: J Org Chem Date: 2005-08-05 Impact factor: 4.354

6. Iridium-catalyzed enantioselective synthesis of allylic alcohols: silanolates as hydroxide equivalents.

Authors: Isabelle Lyothier; Christian Defieber; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2006-09-18 Impact factor: 15.336

7. Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols.

Authors: Satoshi Ueno; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

8. Palladium-triethylborane-triggered direct and regioselective conversion of allylic alcohols to allyl phenyl sulfones.

Authors: Srivari Chandrasekhar; Vannada Jagadeshwar; Birudaraju Saritha; Cheryala Narsihmulu
Journal: J Org Chem Date: 2005-08-05 Impact factor: 4.354

9. Regio- and enantioselective N-allylations of imidazole, benzimidazole, and purine heterocycles catalyzed by single-component metallacyclic iridium complexes.

Authors: Levi M Stanley; John F Hartwig
Journal: J Am Chem Soc Date: 2009-07-01 Impact factor: 15.419

10. Direct, intermolecular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines.

Authors: Daniel J Weix; Dean Marković; Mitsuhiro Ueda; John F Hartwig
Journal: Org Lett Date: 2009-07-02 Impact factor: 6.005

10 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. 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

Review 3. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.

Authors: Raju Jannapu Reddy; Arram Haritha Kumari
Journal: RSC Adv Date: 2021-03-01 Impact factor: 3.361

4. 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

5. Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.

Authors: Wenyong Chen; John F Hartwig
Journal: J Am Chem Soc Date: 2012-09-11 Impact factor: 15.419

6. Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: catalytic enantioselective synthesis of secondary sulfonamides and sulfones.

Authors: Junwon Choi; Pablo Martín-Gago; Gregory C Fu
Journal: J Am Chem Soc Date: 2014-08-15 Impact factor: 15.419

10. Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications.

Authors: Muhammad Salman; Yaoyao Xu; Shahid Khan; Junjie Zhang; Ajmal Khan
Journal: Chem Sci Date: 2020-05-06 Impact factor: 9.825

10 in total

Iridium-catalyzed, regio- and enantioselective allylic substitution with aromatic and aliphatic sulfinates.

1. Regio- and enantioselective allylic amination of achiral allylic esters catalyzed by an iridium-phosphoramidite complex.

2. Synthesis of trisubstituted alkenes via olefin cross-metathesis.

3. Pd-catalyzed enantioselective allylic substitution: new strategic options for the total synthesis of natural products.

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

5. Practical Pd/C-mediated allylic substitution in water.

6. Iridium-catalyzed enantioselective synthesis of allylic alcohols: silanolates as hydroxide equivalents.

7. Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols.

8. Palladium-triethylborane-triggered direct and regioselective conversion of allylic alcohols to allyl phenyl sulfones.

9. Regio- and enantioselective N-allylations of imidazole, benzimidazole, and purine heterocycles catalyzed by single-component metallacyclic iridium complexes.

10. Direct, intermolecular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines.

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

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

Review 3. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.

4. Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

5. Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.

6. Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: catalytic enantioselective synthesis of secondary sulfonamides and sulfones.

7. Copper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling.

8. Palladium-catalyzed regioselective hydrosulfonylation of allenes with sulfinic acids.

9. Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter.

10. Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications.

Review 3. Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Review 3. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.