Nitrene‐Mediated Enantioselective Intramolecular Olefin Oxyamination to Access Chiral γ‐Aminomethyl‐γ‐Lactones

Author:

Nie Xin1,Ritter Clayton W.2,Hemming Marcel1,Ivlev Sergei I.1,Xie Xiulan1,Chen Shuming2,Meggers Eric1ORCID

Affiliation:

1. Fachbereich Chemie Philipps-Universität Marburg Hans-Meerwein-Straße 35043 Marburg Germany

2. College of Arts & Sciences Oberlin College Science Center N381 119 Woodland St. Oberlin OH-44074 USA

Abstract

AbstractAttaching a nitrene precursor to an intramolecular nucleophile allows for a catalytic asymmetric intramolecular oxyamination of alkenes in which the nucleophile adds in an endocyclic position and the amine in an exocyclic fashion. Using chiral‐at‐ruthenium catalysts, chiral γ‐aminomethyl‐γ‐lactones containing a quaternary carbon in γ‐position are provided in high yields (up to 99 %) and with excellent enantioselectivities (up to 99 % ee). DFT calculations support the possibility of both a singlet (concerted oxyamination of the alkene) and triplet pathway (stepwise oxyamination) for the formation of the predominant stereoisomer. γ‐Aminomethyl‐γ‐lactones are versatile chiral building blocks and can be converted to other heterocycles such as δ‐lactams, 2‐oxazolidinones, and tetrahydrofurans.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Wiley

Subject

General Medicine

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