The intramolecular tandem Michael/Mannich-type reaction of α,β-unsaturated carbonyl compounds with acyliminium ions provides access to chiral indolizidines |
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Institution: | Tokyo University of Pharmacy and Life Sciences, School of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan |
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Abstract: | The intramolecular tandem Michael/Mannich-type (Michael addition/halo-Mannich-type) reaction using TiCl4/n-Bu4NI system between the α,β-unsaturated carbonyl compounds possessing an Evans oxazolidinone as a chiral auxiliary and N-acyliminium ion intermediates is described. The reaction was promoted in a mixed solvent of AcOEt–CH2Cl2 to afford indolizidine compounds with three stereogenic centers. |
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