Synlett 2017; 28(11): 1363-1367
DOI: 10.1055/s-0036-1558971
letter
© Georg Thieme Verlag Stuttgart · New York

Design of Novel Hydrogen-Bonding Donor Organocatalysts and Their Application to Asymmetric Direct Aldol Reaction

Hiroshi Akutsu
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Kosuke Nakashima
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Hikaru Yanai
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Akira Kotani
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Shin-ichi Hirashima
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Tomoyuki Yamamoto
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Ryuta Takahashi
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Akihiro Yoshida
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Yuji Koseki
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Hideki Hakamata
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Takashi Matsumoto
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
,
Tsuyoshi Miura*
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: tmiura@toyaku.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 02 February 2017

Accepted after revision: 23 February 2017

Publication Date:
15 March 2017 (online)


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Abstract

Asymmetric catalytic activities of various organocatalysts bearing double hydrogen-bonding donor units showing different pK a values were examined for direct aldol reactions of cyclohexanone with aromatic aldehydes. Organocatalyst with motif exhibiting the highest acidity resulted in the corresponding aldol products with the highest enantioselectivity. A good correlation has been observed between the asymmetric catalytic activity for direct aldol reactions and acidities of double hydrogen-bonding donating units.

Supporting Information