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: robinchi
ntu.edu.sg
S. Chen, L. Hao, Y. Zhang, B. Tiwari, Y. R. Chi, Org. Lett., 2013, 15, 5822-5825.
DOI: 10.1021/ol402877n
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-dihydro-2-pyridinones, lactams, organocatalysis
ID: J54-Y2013
