Journal
CHEMCATCHEM
Volume 4, Issue 7, Pages 959-962Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201200161
Keywords
asymmetric reaction; calculation; Michael reaction; organocatalysis
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (Japan)
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Among 1,4-addition and 1,6-addition reactions, 1,4-addition reaction is the main reaction mode in the Michael reaction of a,beta-?,d-diunsaturated aldehyde with several nucleophiles catalyzed by diphenylprolinol silyl ether via iminium ion intermediate. The 1,4-addition products, which possess excellent enantioselectivity and alkene moiety, are useful chiral building blocks. The ab initio calculation indicates that 1,4-addition reaction is preferable in terms of p-orbital coefficient and Mulliken/CHelpG atomic charge.
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