Direct access to N-unprotected tetrasubstituted propargylamines via direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines
Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N-unprotected alpha-tetr...
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| Published in | Chemical communications (Cambridge, England) Vol. 53; no. 47; pp. 6319 - 6322 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
2017
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| Abstract | Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N-unprotected alpha-tetrasubstituted primary amines without additional deprotection steps. |
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| AbstractList | Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N-unprotected α-tetrasubstituted primary amines without additional deprotection steps. Direct catalytic alkynylation of N -unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N -unprotected α-tetrasubstituted primary amines without additional deprotection steps. Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N-unprotected alpha -tetrasubstituted primary amines without additional deprotection steps. |
| Author | Ohshima, Takashi Morimoto, Hiroyuki Morisaki, Kazuhiro |
| Author_xml | – sequence: 1 givenname: Kazuhiro orcidid: 0000-0002-5692-4726 surname: Morisaki fullname: Morisaki, Kazuhiro organization: Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, Maidashi 3-1-1, Fukuoka 8128582, Japan – sequence: 2 givenname: Hiroyuki orcidid: 0000-0003-4172-2598 surname: Morimoto fullname: Morimoto, Hiroyuki email: hmorimot@phar.kyushu-u.ac.jp organization: Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, Maidashi 3-1-1, Fukuoka 8128582, Japan – sequence: 3 givenname: Takashi orcidid: 0000-0001-9817-6984 surname: Ohshima fullname: Ohshima, Takashi email: ohshima@phar.kyushu-u.ac.jp organization: Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, Maidashi 3-1-1, Fukuoka 8128582, Japan |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28447089$$D View this record in MEDLINE/PubMed |
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| Keywords | AMINATION ASYMMETRIC ALKYNYLATION HYDROGENATION HIGHLY ENANTIOSELECTIVE CONSTRUCTION ARYL HALIDES ARYLATION BOND FORMATION ALDEHYDES EFFICIENT ALPHA-AMINOALLYLATION |
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| Snippet | Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and... Direct catalytic alkynylation of N -unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and... |
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| Title | Direct access to N-unprotected tetrasubstituted propargylamines via direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines |
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