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

^*Corresponding author for this work

Microbial Chemistry Research Foundation

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

20 Scopus citations

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
State	Published - 2019
Externally published	Yes

Keywords

Mannich reaction
asymmetric catalysis
copper catalysis
fluorine
heterocycle

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10.1055/s-0037-1611642

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

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

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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 - 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 - Mannich reaction

KW - asymmetric catalysis

KW - copper catalysis

KW - fluorine

KW - heterocycle

UR - https://www.scopus.com/pages/publications/85061939730

U2 - 10.1055/s-0037-1611642

DO - 10.1055/s-0037-1611642

M3 - 文章

AN - SCOPUS:85061939730

SN - 0936-5214

VL - 30

SP - 488

EP - 492

JO - Synlett

JF - Synlett

IS - 4

ER -

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

Abstract

Keywords

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