Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins

Madhu Chennapuram; U. V. Subba Reddy; Chigusa Seki; Yuko Okuyama; Eunsang Kwon; Koji Uwai; Michio Tokiwa; Mitsuhiro Takeshita; Hiroto Nakano

doi:10.1002/ejoc.201700138

Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins

Madhu Chennapuram, U. V. Subba Reddy, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

SCI - Research and Analytical Center for Giant Molecules

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

A series of hybrid-type squaramide-fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro-aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3-substituted 3-hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee). The resulting chiral 3-hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.

Original language	English
Pages (from-to)	1638-1646
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.201700138
Publication status	Published - 2017 Mar 27

Keywords

Amino alcohols
Asymmetric catalysis
Enantioselectivity
Nitro-aldol reaction
Organocatalysts

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins. / Chennapuram, Madhu; Subba Reddy, U. V.; Seki, Chigusa; Okuyama, Yuko; Kwon, Eunsang; Uwai, Koji; Tokiwa, Michio; Takeshita, Mitsuhiro; Nakano, Hiroto.

In: European Journal of Organic Chemistry, Vol. 2017, No. 12, 27.03.2017, p. 1638-1646.

Research output: Contribution to journal › Article › peer-review

Chennapuram, Madhu ; Subba Reddy, U. V. ; Seki, Chigusa ; Okuyama, Yuko ; Kwon, Eunsang ; Uwai, Koji ; Tokiwa, Michio ; Takeshita, Mitsuhiro ; Nakano, Hiroto. / Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 12. pp. 1638-1646.

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abstract = "A series of hybrid-type squaramide-fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro-aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3-substituted 3-hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee). The resulting chiral 3-hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.",

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AU - Seki, Chigusa

AU - Okuyama, Yuko

AU - Kwon, Eunsang

AU - Uwai, Koji

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AU - Takeshita, Mitsuhiro

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AB - A series of hybrid-type squaramide-fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro-aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3-substituted 3-hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee). The resulting chiral 3-hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.

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KW - Nitro-aldol reaction

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Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins

Abstract

Keywords

ASJC Scopus subject areas

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