Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF                          3                          Amide to Isatin Imines

Jin Sheng Yu; Hidetoshi Noda; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1055/s-0037-1611642

Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF ₃ Amide to Isatin Imines

Jin Sheng Yu, Hidetoshi Noda, Naoya Kumagai, Masakatsu Shibasaki

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

15 Citations (Scopus)

Abstract

An α-CF ₃ amide underwent direct asymmetric Mannich-type reaction to isatin imines in the presence of a chiral catalyst comprising a soft Lewis acid Cu(I), a chiral bisphosphine ligand, and Barton's base. The Mannich adduct was converted in one step into a unique tricycle bearing a trifluoromethylated chiral center and an α-tertiary amine moiety.

Original language	English
Pages (from-to)	488-492
Number of pages	5
Journal	Synlett
Volume	30
Issue number	4
DOIs	https://doi.org/10.1055/s-0037-1611642
Publication status	Published - 2019
Externally published	Yes

Keywords

asymmetric catalysis
copper catalysis
fluorine
heterocycle
Mannich reaction

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-0037-1611642

Cite this

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title = " Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF 3 Amide to Isatin Imines ",

abstract = " An α-CF 3 amide underwent direct asymmetric Mannich-type reaction to isatin imines in the presence of a chiral catalyst comprising a soft Lewis acid Cu(I), a chiral bisphosphine ligand, and Barton's base. The Mannich adduct was converted in one step into a unique tricycle bearing a trifluoromethylated chiral center and an α-tertiary amine moiety. ",

keywords = "asymmetric catalysis, copper catalysis, fluorine, heterocycle, Mannich reaction",

author = "Yu, {Jin Sheng} and Hidetoshi Noda and Naoya Kumagai and Masakatsu Shibasaki",

note = "Funding Information: This work was financially supported by the ACT-C program (JPM-JCR12YO) from JST and KAKENHI (17H03025, JP18K14878, and 18H04276 in Precisely Designed Catalysts with Customized Scaffold- ing) from JSPS and MEXT. J.-S.Y. was supported by a JSPS International Research Fellowship.() Publisher Copyright: {\textcopyright} Georg Thieme Verlag.",

year = "2019",

doi = "10.1055/s-0037-1611642",

language = "English",

volume = "30",

pages = "488--492",

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T1 - Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF 3 Amide to Isatin Imines

AU - Yu, Jin Sheng

AU - Noda, Hidetoshi

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

N1 - Funding Information: This work was financially supported by the ACT-C program (JPM-JCR12YO) from JST and KAKENHI (17H03025, JP18K14878, and 18H04276 in Precisely Designed Catalysts with Customized Scaffold- ing) from JSPS and MEXT. J.-S.Y. was supported by a JSPS International Research Fellowship.() Publisher Copyright: © Georg Thieme Verlag.

PY - 2019

Y1 - 2019

N2 - An α-CF 3 amide underwent direct asymmetric Mannich-type reaction to isatin imines in the presence of a chiral catalyst comprising a soft Lewis acid Cu(I), a chiral bisphosphine ligand, and Barton's base. The Mannich adduct was converted in one step into a unique tricycle bearing a trifluoromethylated chiral center and an α-tertiary amine moiety.

AB - An α-CF 3 amide underwent direct asymmetric Mannich-type reaction to isatin imines in the presence of a chiral catalyst comprising a soft Lewis acid Cu(I), a chiral bisphosphine ligand, and Barton's base. The Mannich adduct was converted in one step into a unique tricycle bearing a trifluoromethylated chiral center and an α-tertiary amine moiety.

KW - asymmetric catalysis

KW - copper catalysis

KW - fluorine

KW - heterocycle

KW - Mannich reaction

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