Synthesis of a Conformationally Stable Atropisomeric Pair of Biphenyl Scaffold Containing Additional Stereogenic Centers

Autor:	Chi-Tung Yeung, Wesley Ting Kwok Chan, Wai-Sum Lo, Ga-Lai Law, Wing-Tak Wong
Jazyk:	angličtina
Rok vydání:	2019
Předmět:	atropisomer asymmetry hydrogen bond N-nitroso aldol reaction Organic chemistry QD241-441
Zdroj:	Molecules, Vol 24, Iss 3, p 643 (2019)
Druh dokumentu:	article
ISSN:	1420-3049 24030643
DOI:	10.3390/molecules24030643
Popis:	The synthesis of a new CF3-containing stereogenic atropisomeric pair of ortho-disubstituted biphenyl scaffold is presented. The atropisomers are surprisingly conformationally stable for isolation. X-ray structures show that their stability comes from an intramolecular hydrogen bond formation from their two hydroxyl groups and renders the spatial arrangement of their peripheral CF3 and CH3 groups very different. The synthesized stereogenic scaffold proved to be effective in catalyzing the asymmetric N-nitroso aldol reaction of enamine and nitrosobenzene. Compared to similar scaffolds without CF3 groups, one of our atropisomer exhibits an increase in enantioselectivity in this reaction.
Databáze:	Directory of Open Access Journals
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