Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

Teppei Otsuki; Jun Kumagai; Yoshihito Kohari; Yuko Okuyama; Eunsang Kwon; Chigusa Seki; Koji Uwai; Yasuteru Mawatari; Nagao Kobayashi; Tatsuo Iwasa; Michio Tokiwa; Mitsuhiro Takeshita; Atushi Maeda; Akihiko Hashimoto; Kana Turuga; Hiroto Nakano

doi:10.1002/ejoc.201500926

Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

Teppei Otsuki, Jun Kumagai, Yoshihito Kohari, Yuko Okuyama, Eunsang Kwon, Chigusa Seki, Koji Uwai, Yasuteru Mawatari, Nagao Kobayashi, Tatsuo Iwasa, Michio Tokiwa, Mitsuhiro Takeshita, Atushi Maeda, Akihiko Hashimoto, Kana Turuga, Hiroto Nakano

SCI - Research and Analytical Center for Giant Molecules

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

27 Citations (Scopus)

Abstract

The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.

Original language	English
Pages (from-to)	7292-7300
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	33
DOIs	https://doi.org/10.1002/ejoc.201500926
Publication status	Published - 2015 Nov 1

Keywords

Amino alcohols
Cycloaddition
Diastereoselectivity
Enantioselectivity
Nitrogen heterocycles
Organocatalysis

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10.1002/ejoc.201500926

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Otsuki, T., Kumagai, J., Kohari, Y., Okuyama, Y., Kwon, E., Seki, C., Uwai, K., Mawatari, Y., Kobayashi, N., Iwasa, T., Tokiwa, M., Takeshita, M., Maeda, A., Hashimoto, A., Turuga, K., & Nakano, H. (2015). Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes. European Journal of Organic Chemistry, 2015(33), 7292-7300. https://doi.org/10.1002/ejoc.201500926

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title = "Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes",

abstract = "The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.",

keywords = "Amino alcohols, Cycloaddition, Diastereoselectivity, Enantioselectivity, Nitrogen heterocycles, Organocatalysis",

author = "Teppei Otsuki and Jun Kumagai and Yoshihito Kohari and Yuko Okuyama and Eunsang Kwon and Chigusa Seki and Koji Uwai and Yasuteru Mawatari and Nagao Kobayashi and Tatsuo Iwasa and Michio Tokiwa and Mitsuhiro Takeshita and Atushi Maeda and Akihiko Hashimoto and Kana Turuga and Hiroto Nakano",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = nov,

day = "1",

doi = "10.1002/ejoc.201500926",

language = "English",

volume = "2015",

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journal = "European Journal of Organic Chemistry",

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Otsuki, T, Kumagai, J, Kohari, Y, Okuyama, Y, Kwon, E, Seki, C, Uwai, K, Mawatari, Y, Kobayashi, N, Iwasa, T, Tokiwa, M, Takeshita, M, Maeda, A, Hashimoto, A, Turuga, K & Nakano, H 2015, 'Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes', European Journal of Organic Chemistry, vol. 2015, no. 33, pp. 7292-7300. https://doi.org/10.1002/ejoc.201500926

TY - JOUR

T1 - Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

AU - Otsuki, Teppei

AU - Kumagai, Jun

AU - Kohari, Yoshihito

AU - Okuyama, Yuko

AU - Kwon, Eunsang

AU - Seki, Chigusa

AU - Uwai, Koji

AU - Mawatari, Yasuteru

AU - Kobayashi, Nagao

AU - Iwasa, Tatsuo

AU - Tokiwa, Michio

AU - Takeshita, Mitsuhiro

AU - Maeda, Atushi

AU - Hashimoto, Akihiko

AU - Turuga, Kana

AU - Nakano, Hiroto

PY - 2015/11/1

Y1 - 2015/11/1

N2 - The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.

AB - The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.

KW - Amino alcohols

KW - Cycloaddition

KW - Diastereoselectivity

KW - Enantioselectivity

KW - Nitrogen heterocycles

KW - Organocatalysis

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U2 - 10.1002/ejoc.201500926

DO - 10.1002/ejoc.201500926

M3 - Article

AN - SCOPUS:84947474874

SN - 1434-193X

VL - 2015

SP - 7292

EP - 7300

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 33

ER -

Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

Abstract

Keywords

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