» Articles » PMID: 15957893

Enantioselective Rhodium Enolate Protonations. A New Methodology for the Synthesis of Beta2-amino Acids

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2005 Jun 17
PMID 15957893
Citations 11
Authors
Affiliations
Soon will be listed here.
Abstract

[reaction: see text] Rhodium-catalyzed conjugate addition of an aryl boronic acid to alpha-methylamino acrylates followed by enantioselective protonation of the oxa-pi-allylrhodium intermediate provides access to aryl-substituted beta(2)-amino acids. The impact of the different variables of the reaction on the levels of enantioselectivity has been assessed.

Citing Articles

α-(Aminomethyl)acrylates as acceptors in radical-polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping.

Palillero-Cisneros A, Gordillo-Guerra P, Garcia-Alvarez F, Jackowski O, Ferreira F, Chemla F Beilstein J Org Chem. 2023; 19:1443-1451.

PMID: 37767333 PMC: 10520473. DOI: 10.3762/bjoc.19.103.


Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride.

Gu Y, Norton J, Salahi F, Lisnyak V, Zhou Z, Snyder S J Am Chem Soc. 2021; 143(25):9657-9663.

PMID: 34142805 PMC: 9366878. DOI: 10.1021/jacs.1c04683.


Conjugate addition-enantioselective protonation reactions.

Phelan J, Ellman J Beilstein J Org Chem. 2016; 12:1203-28.

PMID: 27559372 PMC: 4979737. DOI: 10.3762/bjoc.12.116.


Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

Gigant N, Quintin F, Backvall J J Org Chem. 2015; 80(5):2796-803.

PMID: 25653084 PMC: 4354172. DOI: 10.1021/acs.joc.5b00148.


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

Filloux C, Rovis T J Am Chem Soc. 2014; 137(1):508-17.

PMID: 25545834 PMC: 4304441. DOI: 10.1021/ja511445x.


References
1.
Hayashi T, Takahashi M, Takaya Y, Ogasawara M . Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids. Arylrhodium, oxa-pi-allylrhodium, and hydroxorhodium intermediates. J Am Chem Soc. 2002; 124(18):5052-8. DOI: 10.1021/ja012711i. View

2.
Sibi M, Patil K . Enantioselective H-atom transfer reactions: a new methodology for the synthesis of beta2-amino acids. Angew Chem Int Ed Engl. 2004; 43(10):1235-8. DOI: 10.1002/anie.200353000. View

3.
Fagnou K, Lautens M . Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds. Chem Rev. 2003; 103(1):169-96. DOI: 10.1021/cr020007u. View

4.
Jeulin S, de Paule S, Ratovelomanana-Vidal V, Genet J, Champion N, Dellis P . Chiral biphenyl diphosphines for asymmetric catalysis: stereoelectronic design and industrial perspectives. Proc Natl Acad Sci U S A. 2004; 101(16):5799-804. PMC: 395988. DOI: 10.1073/pnas.0307620101. View

5.
Subbaraju G, Golakoti T, Patterson G, Moore R . Three new cryptophycins from Nostoc sp. GSV 224. J Nat Prod. 1997; 60(3):302-5. DOI: 10.1021/np960700a. View