2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins

Rei Togashi; Madhu Chennapuram; Chigusa Seki; Yuko Okuyama; Eunsang Kwon; Koji Uwai; Michio Tokiwa; Mitsuhiro Takeshita; Hiroto Nakano

doi:10.1002/ejoc.201900308

2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins

Rei Togashi, Madhu Chennapuram, 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

5 Citations (Scopus)

Abstract

New optically active 2-azanorbornane-based amino alcohol organocatalysts were designed and synthesized, and these catalysts were successfully employed in the asymmetric Michael reaction of β-keto esters with nitroolefins to obtain the corresponding chiral Michael adducts with both high chemical yields (up to 99 %) and high stereoselectivities (up to dr = 91:9, up to 91 % ee).

Original language	English
Pages (from-to)	3882-3889
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	24
DOIs	https://doi.org/10.1002/ejoc.201900308
Publication status	Published - 2019 Jun 30

Keywords

2-Azanorbornane
Amino alcohols
Asymmetric reaction
Michael addition
Organocatalyst

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201900308

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title = "2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins",

abstract = "New optically active 2-azanorbornane-based amino alcohol organocatalysts were designed and synthesized, and these catalysts were successfully employed in the asymmetric Michael reaction of β-keto esters with nitroolefins to obtain the corresponding chiral Michael adducts with both high chemical yields (up to 99 %) and high stereoselectivities (up to dr = 91:9, up to 91 % ee).",

keywords = "2-Azanorbornane, Amino alcohols, Asymmetric reaction, Michael addition, Organocatalyst",

author = "Rei Togashi and Madhu Chennapuram and Chigusa Seki and Yuko Okuyama and Eunsang Kwon and Koji Uwai and Michio Tokiwa and Mitsuhiro Takeshita and Hiroto Nakano",

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doi = "10.1002/ejoc.201900308",

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AU - Togashi, Rei

AU - Chennapuram, Madhu

AU - Seki, Chigusa

AU - Okuyama, Yuko

AU - Kwon, Eunsang

AU - Uwai, Koji

AU - Tokiwa, Michio

AU - Takeshita, Mitsuhiro

AU - Nakano, Hiroto

N1 - Funding Information: A part of this research is partially supported by the Adaptable & Seam-less Technology Transfer Program through Target-driven R&D from Japan Science and Technology Agency (JST) (AS231Z01382G). Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/6/30

Y1 - 2019/6/30

N2 - New optically active 2-azanorbornane-based amino alcohol organocatalysts were designed and synthesized, and these catalysts were successfully employed in the asymmetric Michael reaction of β-keto esters with nitroolefins to obtain the corresponding chiral Michael adducts with both high chemical yields (up to 99 %) and high stereoselectivities (up to dr = 91:9, up to 91 % ee).

AB - New optically active 2-azanorbornane-based amino alcohol organocatalysts were designed and synthesized, and these catalysts were successfully employed in the asymmetric Michael reaction of β-keto esters with nitroolefins to obtain the corresponding chiral Michael adducts with both high chemical yields (up to 99 %) and high stereoselectivities (up to dr = 91:9, up to 91 % ee).

KW - 2-Azanorbornane

KW - Amino alcohols

KW - Asymmetric reaction

KW - Michael addition

KW - Organocatalyst

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JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

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ER -

2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins

Abstract

Keywords

ASJC Scopus subject areas

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