Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines

Autor: Jiawei Rong, Juan F. Collados, Pablo Ortiz, Ravindra P. Jumde, Edwin Otten, Syuzanna R. Harutyunyan

Publikováno v: Nature Communications, Vol 7, Iss 1, Pp 1-7 (2016)

The stereoselective addition of Grignard reagents to ketimines is potentially a straightforward route to α-chiral amines. Here the authors report a catalytic, asymmetric Grignard addition to silyl ketimines, givingN-sulfonyl protected α-chiral sily

Externí odkaz: https://doaj.org/article/21be2c4928f94b7f9adb7908f0ebc4c3

Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

Autor: Valentin Paul Nicu, Wybren Jan Buma, Juana M. Pérez, Yiyin Xia, Syuzanna R. Harutyunyan, Mark A. J. Koenis, Juan F. Collados, Pablo Ortiz

Publikováno v: European Journal of Organic Chemistry. 2018:3900-3903

The Brook rearrangement of simple, chiral tertiary benzylic -hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-B

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::f2399e2f472b75d3ce66906cceda3903
https://doi.org/10.1002/ejoc.201701469

Diastereoselective synthesis of 3,4-disubstituted 5-( p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones: chirality transfer in the enantioselective synthesis of ethyl (+)-(3 S,4a S,7a S)-1-oxo-octahydro-1 H-cyclopenta[ c]pyridine-3-carboxylate

Autor: Acherki, Hassan, Alvarez-Ibarra, Carlos, Luján, Juan F. Collados, Quiroga-Feijóo, María L.

Publikováno v: In Tetrahedron: Asymmetry 2005 16(24):4034-4044

Catalytic Synthesis of Enantiopure Chiral Alcohols via Addition of Grignard Reagents to Carbonyl Compounds

Autor: Syuzanna R. Harutyunyan, Ricard Solà, Beatriz Maciá, Juan F. Collados

Publikováno v: ACS Catalysis, 6(3), 1952-1970. AMER CHEMICAL SOC

© 2016 American Chemical Society.Remarkable progress in the enantioselective addition of Grignard reagents to carbonyl compounds has been made over the past decade. This enantioselective transformation now allows the use of these challenging reactiv

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5b80d438093f485ee8151e815bbd68dc
https://hdl.handle.net/11370/d79fc717-7120-4ff4-ae31-f7d166057132

Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides

Autor: Mamen Rodríguez-Fernández, Paul B. White, Xingchen Yan, Syuzanna R. Harutyunyan, Juan F. Collados

Publikováno v: Journal of the American Chemical Society, 139, 40, pp. 14224-14231
Journal of the American Chemical Society, 139(40):jacs.7b07344, 14224-14231. AMER CHEMICAL SOC
Journal of the American Chemical Society
Journal of the American Chemical Society, 139, 14224-14231

Here we report that readily available silyl- and boron-based Lewis acids in combination with chiral copper catalysts are able to overcome the reactivity issues of unactivated enamides, known as the least reactive carboxylic acid derivatives, toward a

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6f133ebfcb0b4f7ca50a2d9261a9e3b2
https://hdl.handle.net/2066/201469