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 in | Organic letters Vol. 20; no. 15; pp. 4490 - 4494 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
03.08.2018
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. 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. 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. |
| Author | Ozaki, Seiya Iwasa, Seiji Chanthamath, Soda Le, Chi Thi Loan Shibatomi, Kazutaka |
| AuthorAffiliation | Department of Environmental and Life Sciences |
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| Author_xml | – sequence: 1 givenname: Chi Thi Loan orcidid: 0000-0001-7793-6841 surname: Le fullname: Le, Chi Thi Loan – sequence: 2 givenname: Seiya surname: Ozaki fullname: Ozaki, Seiya – sequence: 3 givenname: Soda surname: Chanthamath fullname: Chanthamath, Soda – sequence: 4 givenname: Kazutaka orcidid: 0000-0001-6368-4823 surname: Shibatomi fullname: Shibatomi, Kazutaka – sequence: 5 givenname: Seiji surname: Iwasa fullname: Iwasa, Seiji email: Iwasa@ens.tut.ac.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29992821$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_ccr_2019_213051 crossref_primary_10_1021_acs_oprd_2c00265 crossref_primary_10_1039_C9CC06889A crossref_primary_10_1016_j_tet_2020_131481 crossref_primary_10_1002_adsc_202400146 crossref_primary_10_1002_chem_202303070 crossref_primary_10_1021_acscatal_1c02540 crossref_primary_10_1039_D2QO01912D crossref_primary_10_1021_acs_orglett_0c00050 crossref_primary_10_1021_acs_orglett_9b02692 |
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| Keywords | HIGHLY ENANTIOSELECTIVE SYNTHESIS P PINCER COMPLEX RUTHENIUM PORPHYRINS DEHYDROGENATION AMINES INTRAMOLECULAR CYCLOPROPANATION REACTIONS OLEFINS ALPHA DIAZO-COMPOUNDS STEREOSELECTIVE-SYNTHESIS |
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| Snippet | Novel catalysis involving phosphonomethylation of N-methylaniline and asymmetric cyclopropylphosphonation reactions of N,N-diethylaniline derivatives with... Novel catalysis involving phosphonomethylation of N-methylaniline and asymmetric cyclopropylphosphonation reactions of N,N-diethylaniline derivatives with... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Direct Catalytic Asymmetric Cyclopropylphosphonation Reactions of N,N-Dialkyl Groups of Aniline Derivatives by Ru(II)-Pheox Complex |
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