title: Positive Effect of Water in Asymmetric Direct Aldol Reactions with Primary Amine Organocatalyst: Experimental and Computational Studies.
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.
authors: Laboratory 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.
authors: Shin A
authors: SA
authors: Moteki
authors: Laboratory 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.
authors: Hiroki
authors: H
authors: Maruyama
authors: Laboratory 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.
authors: Keiji
authors: K
authors: Nakayama
authors: Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo, Kyoto, 606-8103, Japan.|School of Ocean, Shandong University, Weihai, 264209, China.
authors: Hai-Bei
authors: HB
authors: Li
authors: Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo, Kyoto, 606-8103, Japan.
authors: Galina
authors: G
authors: Petrova
authors: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan.
authors: Satoshi
authors: S
authors: Maeda
authors: Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo, Kyoto, 606-8103, Japan. morokuma@fukui.kyoto-u.ac.jp.
authors: Keiji
authors: K
authors: Morokuma
authors: Laboratory 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. maruoka@kuchem.kyoto-u.ac.jp.
authors: Keiji
authors: K
authors: Maruoka
keywords: aldol; amine; computation; organocatalysis; water