Synlett 2020; 31(20): 2013-2017
DOI: 10.1055/s-0040-1707302
letter

Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts

Yudai Fujii
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
,
Ryota Nakao
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
,
Saki Sugihara
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
,
Keita Fujita
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
,
Yuya Araki
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
,
Takayuki Kudoh
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
,
Ichiro Hayakawa
b   Graduate School of Integrated Basic Sciences, Nihon University, 3-25-40 Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan
,
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
,
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan   Email: sakakura@okayama-u.ac.jp
› Author Affiliations
This work was supported in part by a Grant-in-Aid for Scientific Research (C) (No. 15K05123) from MEXT, the Naito Foundation, and the Okayama Foundation for Science and Technology.


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Abstract

An enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

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Publication History

Received: 06 August 2020

Accepted after revision: 02 September 2020

Article published online:
07 October 2020

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