Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes

Karabuğa, Şemistan; Çakıcı, Murat; Kazaz, Cavit; Şahin, Ertan; Kılıç, Hamdullah; Ulukanlı, Sabri

doi:10.1039/c1ob06205k

Cited by 8 publications

(2 citation statements)

References 57 publications

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“…The yields and enantiomeric excesses of products 25 varied depending on the catalyst structure and the aldehyde used. In the best cases, the yields reached 99% and the enantiomeric excess was 91% …”

Section: Sulfoximinesmentioning

confidence: 99%

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Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

et al. 2017

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Asymmetric synthesis, in which chiral organocatalysts or metal complexes with chiral ligands are used, has become the most valuable methodology for the preparation of enantiomerically pure organic compounds. Among such catalysts/ligands, a growing number constitute various organosulfur compounds. This Review provides comprehensive and critical information on the plethora of sulfur-based chiral ligands and organocatalysts used in asymmetric synthesis, which have been published within the last 15 years. However, it is confined to the presentation of only those chiral catalysts/ligands that possess a stereogenic sulfur atom and includes sulfoxides, sulfinamides, N-sulfinyl ureas, sulfoximines, and some related S-chiral derivatives.

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Section: Sulfoximinesmentioning

confidence: 99%

“…In the best cases, the yields reached 99% and the enantiomeric excess was 91%. 139 5.5.4. Asymmetric Biginelli Reaction.…”

Section: Aldol-type Reactionsmentioning

confidence: 99%

Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

et al. 2017

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ChemInform Abstract: Synthesis of Chiral Sulfoximines Derived from 3‐Aminoquinazolinones and Their Catalysis of Enantioselective Diethylzinc Addition to Aldehydes.

et al. 2012

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Synthesis of Chiral Sulfoximines Derived from 3-Aminoquinazolinones and TheirCatalysis of Enantioselective Diethylzinc Addition to Aldehydes. -The presented chiral sulfoximine QAS, which can be easily prepared in five steps in a 41% overall yield, shows the best results in the title reaction, cf. the reaction of the compound (Id). -(KARABUGA, S.; CAKICI, M.; KAZAZ, C.; SAHIN, E.; KILIC, H.; ULUKANLI*, S.; Org. Biomol. Chem. 9 (2011) 22, 7887-7896, http://dx.doi.org/10.1039/c1ob06205k ; Dep. Chem., Fac. Sci. Lett., Osmaniye Korkut Ata Univ., TR-80000 Osmaniye, Turk.; Eng.) -C. Gebhardt 15-057

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Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes

et al. 2014

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Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes

Cited by 8 publications

References 57 publications

Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

ChemInform Abstract: Synthesis of Chiral Sulfoximines Derived from 3‐Aminoquinazolinones and Their Catalysis of Enantioselective Diethylzinc Addition to Aldehydes.

Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes

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