A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate

Chonticha Suttibut; Yoshihito Kohari; Ko Igarashi; Hiroto Nakano; Masafumi Hirama; Chigusa Seki; Haruo Matsuyama; Koji Uwai; Nobuhiro Takano; Yuko Okuyama; Kenichi Osone; Mitsuhiro Takeshita; Eunsang Kwon

doi:10.1016/j.tetlet.2011.06.109

A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate

Chonticha Suttibut, Yoshihito Kohari, Ko Igarashi, Hiroto Nakano, Masafumi Hirama, Chigusa Seki, Haruo Matsuyama, Koji Uwai, Nobuhiro Takano, Yuko Okuyama, Kenichi Osone, Mitsuhiro Takeshita, Eunsang Kwon

SCI - Research and Analytical Center for Giant Molecules

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

37 Citations (Scopus)

Abstract

An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins.

Original language	English
Pages (from-to)	4745-4748
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2011.06.109
Publication status	Published - 2011 Sept 14

Keywords

β-Amino alcohol
1,2-Dihydropyridine
Diels-Alder reaction
Isoquinuclidine
Organocatalyst

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10.1016/j.tetlet.2011.06.109

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Suttibut, C., Kohari, Y., Igarashi, K., Nakano, H., Hirama, M., Seki, C., Matsuyama, H., Uwai, K., Takano, N., Okuyama, Y., Osone, K., Takeshita, M., & Kwon, E. (2011). A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate. Tetrahedron Letters, 52(37), 4745-4748. https://doi.org/10.1016/j.tetlet.2011.06.109

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title = "A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate",

abstract = "An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins.",

keywords = "β-Amino alcohol, 1,2-Dihydropyridine, Diels-Alder reaction, Isoquinuclidine, Organocatalyst",

author = "Chonticha Suttibut and Yoshihito Kohari and Ko Igarashi and Hiroto Nakano and Masafumi Hirama and Chigusa Seki and Haruo Matsuyama and Koji Uwai and Nobuhiro Takano and Yuko Okuyama and Kenichi Osone and Mitsuhiro Takeshita and Eunsang Kwon",

note = "Funding Information: This work was partially supported by an Adaptable and Seamless Technology transfer Program grant from the Japan Science and Technology Agency (JST). ",

year = "2011",

month = sep,

day = "14",

doi = "10.1016/j.tetlet.2011.06.109",

language = "English",

volume = "52",

pages = "4745--4748",

journal = "Tetrahedron Letters",

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Suttibut, C, Kohari, Y, Igarashi, K, Nakano, H, Hirama, M, Seki, C, Matsuyama, H, Uwai, K, Takano, N, Okuyama, Y, Osone, K, Takeshita, M & Kwon, E 2011, 'A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate', Tetrahedron Letters, vol. 52, no. 37, pp. 4745-4748. https://doi.org/10.1016/j.tetlet.2011.06.109

A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate. / Suttibut, Chonticha; Kohari, Yoshihito; Igarashi, Ko et al.
In: Tetrahedron Letters, Vol. 52, No. 37, 14.09.2011, p. 4745-4748.

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

TY - JOUR

T1 - A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate

AU - Suttibut, Chonticha

AU - Kohari, Yoshihito

AU - Igarashi, Ko

AU - Nakano, Hiroto

AU - Hirama, Masafumi

AU - Seki, Chigusa

AU - Matsuyama, Haruo

AU - Uwai, Koji

AU - Takano, Nobuhiro

AU - Okuyama, Yuko

AU - Osone, Kenichi

AU - Takeshita, Mitsuhiro

AU - Kwon, Eunsang

N1 - Funding Information: This work was partially supported by an Adaptable and Seamless Technology transfer Program grant from the Japan Science and Technology Agency (JST).

PY - 2011/9/14

Y1 - 2011/9/14

N2 - An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins.

AB - An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins.

KW - β-Amino alcohol

KW - 1,2-Dihydropyridine

KW - Diels-Alder reaction

KW - Isoquinuclidine

KW - Organocatalyst

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M3 - Article

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SN - 0040-4039

VL - 52

SP - 4745

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate

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