Direct catalytic asymmetric vinylogous mannich-type reaction of γ-butenolides with ketimines

Liang Yin; Hisashi Takada; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/anie.201303119

Direct catalytic asymmetric vinylogous mannich-type reaction of γ-butenolides with ketimines

Liang Yin, Hisashi Takada, Naoya Kumagai, Masakatsu Shibasaki

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

67 Citations (Scopus)

Abstract

A cooperative catalyst consisting of a soft Lewis acid and a hard Brønsted base promoted the title reaction. The N-thiophosphinoyl group on the ketimines was critical to surpass the high activation barrier through the soft-soft interaction of sulfur and copper. Mannich adducts with a tetrasubstituted stereogenic center were produced with excellent diastereo- and enantioselectivities. TANIAPHOS= ferrocenyl ligand.

Original language	English
Pages (from-to)	7310-7313
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	28
DOIs	https://doi.org/10.1002/anie.201303119
Publication status	Published - 2013 Jul 8
Externally published	Yes

Keywords

asymmetric catalysis
atom economy
cooperative catalysis
ketimines
synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201303119

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abstract = "A cooperative catalyst consisting of a soft Lewis acid and a hard Br{\o}nsted base promoted the title reaction. The N-thiophosphinoyl group on the ketimines was critical to surpass the high activation barrier through the soft-soft interaction of sulfur and copper. Mannich adducts with a tetrasubstituted stereogenic center were produced with excellent diastereo- and enantioselectivities. TANIAPHOS= ferrocenyl ligand.",

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author = "Liang Yin and Hisashi Takada and Naoya Kumagai and Masakatsu Shibasaki",

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T1 - Direct catalytic asymmetric vinylogous mannich-type reaction of γ-butenolides with ketimines

AU - Yin, Liang

AU - Takada, Hisashi

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2013/7/8

Y1 - 2013/7/8

N2 - A cooperative catalyst consisting of a soft Lewis acid and a hard Brønsted base promoted the title reaction. The N-thiophosphinoyl group on the ketimines was critical to surpass the high activation barrier through the soft-soft interaction of sulfur and copper. Mannich adducts with a tetrasubstituted stereogenic center were produced with excellent diastereo- and enantioselectivities. TANIAPHOS= ferrocenyl ligand.

AB - A cooperative catalyst consisting of a soft Lewis acid and a hard Brønsted base promoted the title reaction. The N-thiophosphinoyl group on the ketimines was critical to surpass the high activation barrier through the soft-soft interaction of sulfur and copper. Mannich adducts with a tetrasubstituted stereogenic center were produced with excellent diastereo- and enantioselectivities. TANIAPHOS= ferrocenyl ligand.

KW - asymmetric catalysis

KW - atom economy

KW - cooperative catalysis

KW - ketimines

KW - synthetic methods

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Direct catalytic asymmetric vinylogous mannich-type reaction of γ-butenolides with ketimines

Abstract

Keywords

ASJC Scopus subject areas

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