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Positive Effect of Water in Asymmetric Direct Aldol Reactions with Primary Amine Organocatalyst: Experimental and
Shin A Moteki1, Hiroki Maruyama1, Keiji Nakayama1
1Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan), Fax: (+81) 75-753-4041.
Abstract:
The origin of higher reactivity in water-accelerated asymmetric aldol reactions with our designed primary amine organocatalyst was elucidated by both computational and experimental methods. As suggested by the calculated transition-state structures for water-promoted imine-enamine isomerization, anti-selective aldol reaction and hemiaminal formation, the rate of this aldol reaction was found experimentally to be even more accelerated by the addition of cis-2-butene-1,4-diol as additive.
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