An Effective Borate-Mediated Approach to 1-Trifluoromethyl-1-hydroxy-3-ketophosphonates, Phosphinates, and Phosphine Oxides / Chizhov Dmitrii L.,Vogel Vera,Tverdomed Sergey N.,Charushin Valery N.,Roeschenthaler Gerd-Volker // SYNLETT. - 2011. - V. , l. 12. - P. 1735-1739.

ISSN/EISSN:

0936-5214 / нет данных

Type:

Article

Abstract:

Ethyl 1-trifluoromethyl-1-hydroxy-3-oxo-phosphonates, the related (methyl)phosphinates and (phenyl) phosphinates, and phosphine oxides were obtained in good yield via direct phosphonylation of acyltrifluoroacetones with diethyl phosphite, ethyl (methyl) phosphonite, ethyl (phenyl) phosphonite, and diphenylphosphine oxide in the presence of triethyl borate. The subsequent dehydration of the selected phosphonates and phosphinates proceeds smoothly affording previously unknown diethyl 1,2-unsaturated 1-trifluoromethyl-3-oxophosphonates, ethyl 1-trifluoromethyl-3-oxo(methyl)-, and ethyl 1-trifluoromethyl-3-oxo(phenyl) phosphinates in good yields.

Author keywords:

acyltrifluoroacetones; phosphonylation; triethyl borate; fluorinated phosphonate; fluorinated phosphinate; fluorinated phosphine oxides ORGANOCATALYTIC ENANTIOSELECTIVE SYNTHESIS; POLYKETIDE BIOSYNTHESIS; DERIVATIVES; INHIBITORS; BORON; HYDROXYPHOSPHONATES; PHOSPHONATES; HETEROCYCLES; ROUTE

DOI:

10.1055/s-0030-1260935

Web of Science ID:

ISI:000292596600020

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JUL
Publisher	GEORG THIEME VERLAG KG
Address	RUDIGERSTR 14, D-70469 STUTTGART, GERMANY
Language	English
Keywords-Plus	ORGANOCATALYTIC ENANTIOSELECTIVE SYNTHESIS; POLYKETIDE BIOSYNTHESIS; DERIVATIVES; INHIBITORS; BORON; HYDROXYPHOSPHONATES; PHOSPHONATES; HETEROCYCLES; ROUTE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dlchizhov@ios.uran.ru
Funding-Acknowledgement	Deutsche Forschungsgemeinschaft {[}DFG 436 RUS 113/911/0-1]
Funding-Text	D.L.C. is grateful to the Deutsche Forschungsgemeinschaft for generous financial support (Grant DFG 436 RUS 113/911/0-1).
Number-of-Cited-References	45
Usage-Count-Since-2013	8
Journal-ISO	Synlett
Doc-Delivery-Number	790NV