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3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.


ABSTRACT: Herein, we describe the development of a synthetic strategy towards chiral 3-pyrrolines based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis. This approach takes advantage of commercially available amino acids as chiral pool reagents and FeCl3 as a Lewis acid catalyst. Our strategy is characterized by its operational simplicity, mild reaction conditions and functional group tolerance. Investigations show that an electron-deficient nitrogen protecting group overcomes limitations arising from competitive binding of the Lewis acid catalyst to unfavorable Lewis basic sites, which ultimately enables catalytic turnover.

PROVIDER: S-EPMC6162066 | BioStudies |

REPOSITORIES: biostudies

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