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Asymmetric Access to the Smallest Enolate Intermediate via Organocatalytic Activation of Acetic Ester

Shaojin Chen, Lin Hao, Yuexia Zhang, Bhoopendra Tiwari and Yonggui Robin Chi*

*Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: robinchintu.edu.sg

S. Chen, L. Hao, Y. Zhang, B. Tiwari, Y. R. Chi, Org. Lett., 2013, 15, 5822-5825.

DOI: 10.1021/ol402877n (free Supporting Information)


Abstract

After NHC-catalyzed activation of acetic esters, the catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively.

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Key Words

3,4-dihydropyran-2-ones, lactams, organocatalysis


ID: J54-Y2013