Journal
TETRAHEDRON
Volume 66, Issue 33, Pages 6293-6299Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.05.047
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Funding
- Engineering and Physical Sciences Research Council [EP/E052185/1, EP/D501725/1] Funding Source: researchfish
- EPSRC [EP/E052185/1] Funding Source: UKRI
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An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me2S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.
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