Enantioselective intramolecular C–H amination of aliphatic azides by dual ruthenium and phosphine catalysis
The catalytic enantioselective intramolecular C(sp 3 )-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bi...
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| Published in | Chemical science (Cambridge) Vol. 10; no. 11; pp. 3202 - 3207 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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CAMBRIDGE
Royal Soc Chemistry
21.03.2019
Royal Society of Chemistry |
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| Abstract | The catalytic enantioselective intramolecular C(sp
3
)-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl)phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral α-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid (
R
)-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C–H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C–H aminations of unactivated aliphatic azides. |
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| AbstractList | The catalytic enantioselective intramolecular C(sp(3))-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl) phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral alpha-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid (R)-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C-H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C-H aminations of unactivated aliphatic azides. The catalytic enantioselective intramolecular C(sp 3 )-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl)phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral α-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid ( R )-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C–H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C–H aminations of unactivated aliphatic azides. The catalytic enantioselective intramolecular C(sp3)-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl)phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral α-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid (R)-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C–H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C–H aminations of unactivated aliphatic azides. The catalytic enantioselective intramolecular C(sp )-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl)phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral α-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid ( )-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C-H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C-H aminations of unactivated aliphatic azides. By combining a chiral-at-metal ruthenium catalyst with catalytic amounts of tris( p -fluorophenyl)phosphine (both 1 mol%), the challenging catalytic enantioselective ring-closing C(sp 3 )-H amination of unactivated aliphatic azides has been achieved with high enantioselectivities. The catalytic enantioselective intramolecular C(sp 3 )-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl)phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral α-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid ( R )-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C–H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C–H aminations of unactivated aliphatic azides. The catalytic enantioselective intramolecular C(sp3)-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl)phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral α-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid (R)-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C-H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C-H aminations of unactivated aliphatic azides.The catalytic enantioselective intramolecular C(sp3)-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic amines which constitute a prominent structural motif in bioactive compounds. We report a dual catalytic system involving a chiral-at-metal bis(pyridyl-NHC) ruthenium complex and tris(4-fluorophenyl)phosphine (both 1 mol%), which facilitates the cyclization of aliphatic azides to chiral α-aryl pyrrolidines with enantioselectivities of up to 99% ee, including a pyrrolidine which can be converted to the anti-tumor alkaloid (R)-(+)-crispine. Mechanistically, the phosphine activates the organic azide to form an intermediate iminophosphorane and transfers the nitrene unit to the ruthenium providing an imido ruthenium intermediate which engages in the highly stereocontrolled C-H amination. This dual catalysis combines ruthenium catalysis with the Staudinger reaction and provides a novel strategy for catalyzing enantioselective C-H aminations of unactivated aliphatic azides. |
| Author | Hemming, Marcel Zhou, Zijun Qin, Jie Meggers, Eric Cui, Tianjiao |
| AuthorAffiliation | a Fachbereich Chemie , Philipps-Universität Marburg , Hans-Meerwein-Strasse 4 , 35043 Marburg , Germany . Email: meggers@chemie.uni-marburg.de |
| AuthorAffiliation_xml | – name: a Fachbereich Chemie , Philipps-Universität Marburg , Hans-Meerwein-Strasse 4 , 35043 Marburg , Germany . Email: meggers@chemie.uni-marburg.de |
| Author_xml | – sequence: 1 givenname: Jie surname: Qin fullname: Qin, Jie organization: Fachbereich Chemie, Philipps-Universität Marburg, 35043 Marburg, Germany – sequence: 2 givenname: Zijun surname: Zhou fullname: Zhou, Zijun organization: Fachbereich Chemie, Philipps-Universität Marburg, 35043 Marburg, Germany – sequence: 3 givenname: Tianjiao surname: Cui fullname: Cui, Tianjiao organization: Fachbereich Chemie, Philipps-Universität Marburg, 35043 Marburg, Germany – sequence: 4 givenname: Marcel surname: Hemming fullname: Hemming, Marcel organization: Fachbereich Chemie, Philipps-Universität Marburg, 35043 Marburg, Germany – sequence: 5 givenname: Eric orcidid: 0000-0002-8851-7623 surname: Meggers fullname: Meggers, Eric organization: Fachbereich Chemie, Philipps-Universität Marburg, 35043 Marburg, Germany |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30996902$$D View this record in MEDLINE/PubMed |
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| Issue | 11 |
| Keywords | PHOSPHORYL AZIDES FUNCTIONALIZATION NITRENE TRANSFER PYRROLIDINE BOND AMINATION AZIRIDINATION COMPLEXES ARYL AZIDES C(SP)-H ALKYL AZIDES |
| Language | English |
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| Publisher | Royal Soc Chemistry Royal Society of Chemistry |
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| Snippet | The catalytic enantioselective intramolecular C(sp
3
)-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic... The catalytic enantioselective intramolecular C(sp(3))-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic... The catalytic enantioselective intramolecular C(sp )-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic... The catalytic enantioselective intramolecular C(sp3)-H amination of aliphatic azides represents an efficient method for constructing chiral saturated cyclic... By combining a chiral-at-metal ruthenium catalyst with catalytic amounts of tris( p -fluorophenyl)phosphine (both 1 mol%), the challenging catalytic... |
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| SubjectTerms | Aliphatic compounds Amines Aromatic compounds Azides (organic) Catalysis Chemistry Chemistry, Multidisciplinary Coordination compounds Enantiomers Physical Sciences Ruthenium compounds Science & Technology |
| Title | Enantioselective intramolecular C–H amination of aliphatic azides by dual ruthenium and phosphine catalysis |
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