Formation of Complex α-Imino Esters via Multihetero-Cope Rearrangement­ of α-Keto Ester Derived Nitrones

This work was carried out in the Department of Chemistry at UNC Chapel Hill, which celebrated its bicentennial in 2018.

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

A sequential benzoylation and multihetero-Cope rearrangement of α-keto ester derived nitrones has been developed. The reaction furnishes a diverse array of complex α-imino ester derivatives. The products can be transformed into amino alcohols via LiAlH₄ reduction.

Key words

rearrangement - ketones - imines - oxygenations - esters

• References

• 1 Current address: Enanta Pharmaceuticals, 500 Arsenal Street, Watertown, MA 02472, USA.
• 2 Current address: Elder Research, 14 E Peace St., Suite 302, Raleigh, NC 27604, USA.
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