Asymmetric Syntheses Using Heteroarenesulfonyl Groups as a Highly Functional Protecting-activating Group

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  • Nakamura Shuichi
    Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology
  • Shibata Norio
    Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology
  • Toru Takeshi

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Other Title
  • ヘテロアレーンスルホニル基を高機能性保護·活性化基として利用する不斉合成反応
  • ヘテロアレーンスルホニル基を高機能性保護・活性化基として利用する不斉合成反応
  • ヘテロアレーンスルホニルキ オ コウキノウセイ ホゴ カッセイカキ ト シテ リヨウ スル フセイ ゴウセイ ハンノウ
  • ChemInform Abstract: Asymmetric Syntheses Using Heteroarenesulfonyl Groups as a Highly Functional Protecting‐Activating Group

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Description

Enantioselective bond formation reaction is of great interest to medicinal or material science. In order to develop the synthetic methodology for these compounds, we designed heteroarenesulfonyl groups as an activating group for imines and a protecting group for amines. The heteroarenesulfonyl group was shown to be an efficient protective group, which has notable properties of high chiral inducibility and activation of the imino group toward the addition of several nucleophiles. Furthermore, we designed N-(heteroarenesulfonyl)prolinamides as novel organocatalysts. Enantioselective aldol reaction of acetone or acetaldehyde with various isatin derivatives using N-(2-thiophenesulfonyl)prolinamide afforded convolutamydine derivatives with high enantioselectivity.

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