NDLI: Enantioselective intramolecular C–H amination of aliphatic azides by dual ruthenium and phosphine catalysis† †Electronic supplementary information (ESI) available: Characterization data and experimental procedures. See DOI: 10.1039/c9sc00054b

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Enantioselective intramolecular C–H amination of aliphatic azides by dual ruthenium and phosphine catalysis† †Electronic supplementary information (ESI) available: Characterization data and experimental procedures. See DOI: 10.1039/c9sc00054b

Content Provider	Semantic Scholar
Author	Zhou, Zijun Cui, Tianjiao Hemming, Marcel Meggers, Eric
Copyright Year	2019
Abstract	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.
Starting Page	3202
Ending Page	3207
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/C9SC00054B
PubMed reference number	30996902
Journal	Medline
Volume Number	10
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc00054b?page=search
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc00054b
Alternate Webpage(s)	https://doi.org/10.1039/C9SC00054B
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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Enantioselective intramolecular C-H amination of aliphatic azides by dual ruthenium and phosphine catalysis.

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Enantioselective intramolecular C–H amination of aliphatic azides by dual ruthenium and phosphine catalysis† †Electronic supplementary information (ESI) available: Characterization data and experimental procedures. See DOI: 10.1039/c9sc00054b

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