Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 48, Pages 6670-6673Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202101106
Keywords
Asymmetric reaction; Domino reactions; Formal [4+2] cycloaddition; Michael addition; Organocatalyst
Categories
Funding
- JSPS KAKENHI [JP20H04801, JP19H05630]
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The asymmetric domino Michael/Michael reaction catalyzed by diphenylprolinol silyl ether results in the formation of penta-substituted cyclohexanes with three continuous chiral centers, showing excellent diastereo- and enantioselectivity.
An asymmetric domino Michael/Michael reaction of alpha,beta-unsaturated aldehydes 1 and alpha-acetyl-beta-substituted-alpha,beta-unsaturated esters 2 catalyzed by diphenylprolinol silyl ether was developed. This is a formal carbo [4+2] cycloaddition reaction affording penta-substituted cyclohexanes having the three continuous chiral centers with excellent diastereo- and enantioselectivity.
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