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

Abstract Asymmetric catalytic activities of various organocatalysts bearing double hydrogen-bonding donor units showing different p K a values were examined for direct aldol reactions of cyclohexanone with aromatic aldehydes. Organocatalyst with motif exhibiting the highest acidity resulted in the c...

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Bibliographic Details
Published in:Synlett 2017-07, Vol.28 (11), p.1363-1367
Main Authors: Akutsu, Hiroshi, Nakashima, Kosuke, Yanai, Hikaru, Kotani, Akira, Hirashima, Shin-ichi, Yamamoto, Tomoyuki, Takahashi, Ryuta, Yoshida, Akihiro, Koseki, Yuji, Hakamata, Hideki, Matsumoto, Takashi, Miura, Tsuyoshi
Format: Article
Language:English
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Summary:Abstract Asymmetric catalytic activities of various organocatalysts bearing double hydrogen-bonding donor units showing different p K 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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1558971