Direct Catalytic Asymmetric Cyclopropylphosphonation Reactions of N,N-Dialkyl Groups of Aniline Derivatives by Ru(II)-Pheox Complex

Novel catalysis involving phosphonomethylation of N-methylaniline and asymmetric cyclopropyl­phosphonation reactions of N,N-diethylaniline derivatives with diazomethyl­phosphonates are reported. Optically active cyclopropyl­phosphonate derivatives were directly synthesized from diazomethyl­phosphona...

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Published inOrganic letters Vol. 20; no. 15; pp. 4490 - 4494
Main Authors Le, Chi Thi Loan, Ozaki, Seiya, Chanthamath, Soda, Shibatomi, Kazutaka, Iwasa, Seiji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.08.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HIGHLY ENANTIOSELECTIVE SYNTHESIS
P PINCER COMPLEX
RUTHENIUM PORPHYRINS
DEHYDROGENATION
AMINES
INTRAMOLECULAR CYCLOPROPANATION REACTIONS
OLEFINS
ALPHA
DIAZO-COMPOUNDS
STEREOSELECTIVE-SYNTHESIS
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Summary:Novel catalysis involving phosphonomethylation of N-methylaniline and asymmetric cyclopropyl­phosphonation reactions of N,N-diethylaniline derivatives with diazomethyl­phosphonates are reported. Optically active cyclopropyl­phosphonate derivatives were directly synthesized from diazomethyl­phosphonates and N,N-diethylaniline derivatives catalyzed by a Ru­(II)-Pheox complex in one step in good yields and high diastereoselectivities (up to trans/cis = > 99:1<) and enantioselectivities (up to 99% ee). D-labeling mechanistic studies of phosphono­methylation and cyclopropyl­phosphonation suggested that an enamine or iminium intermediate was generated in the reaction process.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01788