Synlett 2023; 34(16): 1899-1904
DOI: 10.1055/s-0042-1751471
letter

Diarylmethylamine (‘Butterfly’-Type Amine) Unit: A Useful Unit for the Modulation of the Catalytic Activity of Aminothiourea Catalysts

Hiromasa Ogawa
,
Hiroto Okawa
,
Keiji Mori
This work was partially supported by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science.


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Abstract

We investigated the effects of substituents on the aromatic rings in a diarylmethylamine unit (which we have named the ‘butterfly’-type amine unit) in an aminothiourea catalyst. Detailed examination of the electronic effects of the aromatic rings revealed that the catalyst having a 3,5-bis(trifluoromethyl)phenyl group was the best, realizing an excellent chemical yield and enantioselectivity in an asymmetric Michael reaction between nitrostyrene and dimethyl malonate. Importantly, its catalytic ability as a chiral catalyst is superior to that of the well-known aminothiourea catalyst, the Takemoto catalyst, and this characteristic was observed in various asymmetric reactions.

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Publication History

Received: 05 April 2023

Accepted after revision: 23 May 2023

Article published online:
27 June 2023

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