A new type of amino amide organocatalyzed enantioselective crossed aldol reaction of ketones with aromatic aldehydes

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

doi:10.1016/j.tet.2018.07.016

A new type of amino amide organocatalyzed enantioselective crossed aldol reaction of ketones with aromatic aldehydes

Isiaka A. Owolabi, U. V. Subba Reddy, 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

8 Citations (Scopus)

Abstract

A new type of amino amide organocatalysts was designed and synthesized from commercially available amino acids in easy steps. Their catalytic activities were examined in enantioselective crossed aldol reaction of various acyclic and cyclic ketones with aromatic aldehydes to afford the corresponding chiral anti-aldol adducts with good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn:anti = 1:99, up to 97% ee).

Original language	English
Pages (from-to)	4705-4711
Number of pages	7
Journal	Tetrahedron
Volume	74
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2018.07.016
Publication status	Published - 2018 Sep 6

Keywords

Aldehydes
Amino amide
Crossed aldol reaction
Ketones
Organocatalysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2018.07.016

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A new type of amino amide organocatalyzed enantioselective crossed aldol reaction of ketones with aromatic aldehydes. / Owolabi, Isiaka A.; Subba Reddy, U. V.; Chennapuram, Madhu; Seki, Chigusa; Okuyama, Yuko; Kwon, Eunsang; Uwai, Koji; Tokiwa, Michio; Takeshita, Mitsuhiro; Nakano, Hiroto.

In: Tetrahedron, Vol. 74, No. 36, 06.09.2018, p. 4705-4711.

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

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abstract = "A new type of amino amide organocatalysts was designed and synthesized from commercially available amino acids in easy steps. Their catalytic activities were examined in enantioselective crossed aldol reaction of various acyclic and cyclic ketones with aromatic aldehydes to afford the corresponding chiral anti-aldol adducts with good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn:anti = 1:99, up to 97% ee).",

keywords = "Aldehydes, Amino amide, Crossed aldol reaction, Ketones, Organocatalysis",

author = "Owolabi, {Isiaka A.} and {Subba Reddy}, {U. V.} and Madhu Chennapuram and Chigusa Seki and Yuko Okuyama and Eunsang Kwon and Koji Uwai and Michio Tokiwa and Mitsuhiro Takeshita and Hiroto Nakano",

note = "Funding Information: We thank Adaptable & Seamless Technology Transfer Program through Target-driven R&D from Japan Science and Technology Agency (JST) (2016) and Muroran Institute of Technology for partial financial support to this study. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

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AU - Owolabi, Isiaka A.

AU - Subba Reddy, U. V.

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: We thank Adaptable & Seamless Technology Transfer Program through Target-driven R&D from Japan Science and Technology Agency (JST) (2016) and Muroran Institute of Technology for partial financial support to this study. Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/9/6

Y1 - 2018/9/6

N2 - A new type of amino amide organocatalysts was designed and synthesized from commercially available amino acids in easy steps. Their catalytic activities were examined in enantioselective crossed aldol reaction of various acyclic and cyclic ketones with aromatic aldehydes to afford the corresponding chiral anti-aldol adducts with good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn:anti = 1:99, up to 97% ee).

AB - A new type of amino amide organocatalysts was designed and synthesized from commercially available amino acids in easy steps. Their catalytic activities were examined in enantioselective crossed aldol reaction of various acyclic and cyclic ketones with aromatic aldehydes to afford the corresponding chiral anti-aldol adducts with good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn:anti = 1:99, up to 97% ee).

KW - Aldehydes

KW - Amino amide

KW - Crossed aldol reaction

KW - Ketones

KW - Organocatalysis

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SN - 0040-4020

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A new type of amino amide organocatalyzed enantioselective crossed aldol reaction of ketones with aromatic aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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