Among 1,4-addition and 1,6-addition reactions, 1,4-addition reaction is the main reaction mode in the Michael reaction of α,β-γ,δ-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 π-orbital coefficient and Mulliken/CHelpG atomic charge.
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