Abstract
The asymmetric catalytic Mukaiyama Michael reaction between α,β-unsaturated aldehydes and silyl enol ether derived from a cyclic ketone was catalyzed by diphenylprolinol silyl ether to afford Michael products with excellent diastereo- and enantioselectivities. Bicyclo[2.2.2]octanone derivatives can be synthesized as a single isomer in a nearly optically pure form via a two-step, one-pot reaction, comprising the sequential Mukaiyama Michael reaction and intramolecular Michael reaction starting from dienol silyl ether and α,β-unsaturated aldehydes, catalyzed by diphenylprolinol silyl ether. In the second Michael reaction, positive kinetic resolution occurred to increase the enantioselectivity.
Original language | English |
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Pages (from-to) | 5596-5600 |
Number of pages | 5 |
Journal | European Journal of Organic Chemistry |
Volume | 2020 |
Issue number | 34 |
DOIs | |
Publication status | Published - 2020 Sep 14 |
Keywords
- Asymmetric reactions
- Kinetic resolution
- Mukaiyama Michael reaction
- One-pot reactions
- Organocatalysis
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry