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Literature DB >> 15340633

Rhodium catalysed tandem conjugate addition-protonation: an enantioselective synthesis of 2-substituted succinic esters.

Rebecca J Moss¹, Kelly J Wadsworth, Christopher J Chapman, Christopher G Frost.

Abstract

The rhodium catalysed addition of potassium trifluoro(organo)borates to dimethyl itaconate generates an intermediate complex which on protonation provides enantioenriched succinic esters.

Entities: Chemical

Year: 2004 PMID： 15340633 DOI： 10.1039/b406905f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

8 in total

Review 1. Enantioselective protonation.

Authors: Justin T Mohr; Allen Y Hong; Brian M Stoltz
Journal: Nat Chem Date: 2009-08 Impact factor: 24.427

2. Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.

Authors: Madeleine E Kieffer; Lindsay M Repka; Sarah E Reisman
Journal: J Am Chem Soc Date: 2012-03-05 Impact factor: 15.419

3. Enantioselective rhodium enolate protonations. A new methodology for the synthesis of beta2-amino acids.

Authors: Mukund P Sibi; Hiroto Tatamidani; Kalyani Patil
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

4. Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

Authors: Andrew DeAngelis; Valerie W Shurtleff; Olga Dmitrenko; Joseph M Fox
Journal: J Am Chem Soc Date: 2011-01-25 Impact factor: 15.419

5. Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.

Authors: Gary A Molander; Inji Shin; Ludivine Jean-Gérard
Journal: Org Lett Date: 2010-10-01 Impact factor: 6.005

Rhodium catalysed tandem conjugate addition-protonation: an enantioselective synthesis of 2-substituted succinic esters.

Review 1. Enantioselective protonation.

2. Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.

3. Enantioselective rhodium enolate protonations. A new methodology for the synthesis of beta2-amino acids.

4. Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

5. Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.

6. Rh(I)-bisphosphine-catalyzed asymmetric, intermolecular hydroheteroarylation of α-substituted acrylate derivatives.

Review 7. Conjugate addition-enantioselective protonation reactions.

8. Trans-selective rhodium catalysed conjugate addition of organoboron reagents to dihydropyranones.