Enantioseparation of P-Stereogenic Secondary Phosphine Oxides and Their Stereospecific Transformation to Various Tertiary Phosphine Oxides and a Thiophosphinate

Autor:	Tamás Holczbauer, Bence Varga, Réka Herbay, Elemér Fogassy, György Keglevich, Péter Szemesi, Péter Bagi, Petra Nagy
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Enantiopure drug chemistry Aryl Organic Chemistry Phenylphosphine Non-covalent interactions Enantiomeric excess Medicinal chemistry Alkyl Phosphine Stereocenter
Zdroj:	The Journal of Organic Chemistry. 86:14493-14507
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c01364
Popis:	Secondary phosphine oxides incorporating various aryl and alkyl groups were synthesized in racemic form, and these products formed the library reported in this study. TADDOL derivatives were used to obtain the optical resolution of these P-stereogenic secondary phosphine oxides. The developed resolution method showed a good scope under the optimized reaction conditions, as 9 out of 14 derivatives could be prepared with an enantiomeric excess (ee) ≥ 79% and 5 of these derivatives were practically enantiopure >P(O)H compounds (ee ≥ 98%). The scalability of this resolution method was also demonstrated. Noncovalent interactions responsible for the formation of diasteromeric complexes were elucidated by single-crystal XRD measurements. (S)-(2-Methylphenyl)phenylphosphine oxide was transformed to a variety of P-stereogenic tertiary phosphine oxides and a thiophosphinate in stereospecific Michaelis-Becker, Hirao, or Pudovik reactions.
Databáze:	OpenAIRE
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