Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

Toshihisa Takahashi; U. V. Subba Reddy; Yoshihito Kohari; Chigusa Seki; Taniyuki Furuyama; Nagao Kobayashi; Yuko Okuyama; Eunsang Kwon; Koji Uwai; Michio Tokiwa; Mitsuhiro Takeshita; Hiroto Nakano

doi:10.1016/j.tetlet.2016.11.030

Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

Toshihisa Takahashi, U. V. Subba Reddy, Yoshihito Kohari, Chigusa Seki, Taniyuki Furuyama, Nagao Kobayashi, 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

11 Citations (Scopus)

Abstract

The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.

Original language	English
Pages (from-to)	5771-5776
Number of pages	6
Journal	Tetrahedron Letters
Volume	57
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2016.11.030
Publication status	Published - 2016

Keywords

3-Hydroxy-2-pyridone
Diels-Alder reaction
Enantioselective organocatalysis
Primary β-amino alcohol

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10.1016/j.tetlet.2016.11.030

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title = "Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones",

abstract = "The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.",

keywords = "3-Hydroxy-2-pyridone, Diels-Alder reaction, Enantioselective organocatalysis, Primary β-amino alcohol",

author = "Toshihisa Takahashi and {Subba Reddy}, {U. V.} and Yoshihito Kohari and Chigusa Seki and Taniyuki Furuyama and Nagao Kobayashi and Yuko Okuyama and Eunsang Kwon and Koji Uwai and Michio Tokiwa and Mitsuhiro Takeshita and Hiroto Nakano",

note = "Funding Information: This research is partially supported by the Adaptable & Seamless Technology Transfer Program through Target-driven R&D from Japan Science and Technology Agency , JST ( AS231Z01382G ). Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.11.030",

language = "English",

volume = "57",

pages = "5771--5776",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

AU - Takahashi, Toshihisa

AU - Subba Reddy, U. V.

AU - Kohari, Yoshihito

AU - Seki, Chigusa

AU - Furuyama, Taniyuki

AU - Kobayashi, Nagao

AU - Okuyama, Yuko

AU - Kwon, Eunsang

AU - Uwai, Koji

AU - Tokiwa, Michio

AU - Takeshita, Mitsuhiro

AU - Nakano, Hiroto

N1 - Funding Information: This research is partially supported by the Adaptable & Seamless Technology Transfer Program through Target-driven R&D from Japan Science and Technology Agency , JST ( AS231Z01382G ). Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.

AB - The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.

KW - 3-Hydroxy-2-pyridone

KW - Diels-Alder reaction

KW - Enantioselective organocatalysis

KW - Primary β-amino alcohol

UR - http://www.scopus.com/inward/record.url?scp=84997684134&partnerID=8YFLogxK

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U2 - 10.1016/j.tetlet.2016.11.030

DO - 10.1016/j.tetlet.2016.11.030

M3 - Article

AN - SCOPUS:84997684134

SN - 0040-4039

VL - 57

SP - 5771

EP - 5776

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

Abstract

Keywords

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