Preparation of Nd/Na heterogeneous catalyst from bench-stable and inexpensive Nd salt for an anti-selective catalytic asymmetric nitroaldol reaction

Akihito Nonoyama; Kazuki Hashimoto; Akira Saito; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1016/j.tetlet.2016.03.041

Preparation of Nd/Na heterogeneous catalyst from bench-stable and inexpensive Nd salt for an anti-selective catalytic asymmetric nitroaldol reaction

Akihito Nonoyama, Kazuki Hashimoto, Akira Saito, Naoya Kumagai, Masakatsu Shibasaki

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

19 Citations (Scopus)

Abstract

A Nd/Na heterobimetallic complex prepared from an amide-based chiral ligand, Nd alkoxide, and NaHMDS is a highly efficient heterogeneous catalyst for an anti-selective catalytic asymmetric nitroaldol reaction. Nd alkoxide is sensitive to moisture, expensive, and scarce, making it difficult to use the Nd/Na catalyst in large-scale applications. Herein we describe a new protocol that allows for catalyst preparation from bench-stable and inexpensive NdCl₃·6H₂O with comparable catalytic activity.

Original language	English
Pages (from-to)	1815-1819
Number of pages	5
Journal	Tetrahedron Letters
Volume	57
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2016.03.041
Publication status	Published - 2016 Apr 20
Externally published	Yes

Keywords

Bimetallic complex
Enantioselective
Flow reaction
Neodymium
Nitroaldol

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2016.03.041

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title = "Preparation of Nd/Na heterogeneous catalyst from bench-stable and inexpensive Nd salt for an anti-selective catalytic asymmetric nitroaldol reaction",

abstract = "A Nd/Na heterobimetallic complex prepared from an amide-based chiral ligand, Nd alkoxide, and NaHMDS is a highly efficient heterogeneous catalyst for an anti-selective catalytic asymmetric nitroaldol reaction. Nd alkoxide is sensitive to moisture, expensive, and scarce, making it difficult to use the Nd/Na catalyst in large-scale applications. Herein we describe a new protocol that allows for catalyst preparation from bench-stable and inexpensive NdCl3·6H2O with comparable catalytic activity.",

keywords = "Bimetallic complex, Enantioselective, Flow reaction, Neodymium, Nitroaldol",

author = "Akihito Nonoyama and Kazuki Hashimoto and Akira Saito and Naoya Kumagai and Masakatsu Shibasaki",

note = "Funding Information: Acknowledgments This work was financially supported by ACT-C, JST, and KAKENHI (20229001) from JSPS. N.K. thanks the Japan Agency for Medical Research and Development (AMED) for financial support. SCAS (Sumika Chemical Analysis Service) is gratefully thanked for XRD and STEM analyses. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd. All rights reserved.",

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doi = "10.1016/j.tetlet.2016.03.041",

language = "English",

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T1 - Preparation of Nd/Na heterogeneous catalyst from bench-stable and inexpensive Nd salt for an anti-selective catalytic asymmetric nitroaldol reaction

AU - Nonoyama, Akihito

AU - Hashimoto, Kazuki

AU - Saito, Akira

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

N1 - Funding Information: Acknowledgments This work was financially supported by ACT-C, JST, and KAKENHI (20229001) from JSPS. N.K. thanks the Japan Agency for Medical Research and Development (AMED) for financial support. SCAS (Sumika Chemical Analysis Service) is gratefully thanked for XRD and STEM analyses. Publisher Copyright: © 2016 Elsevier Ltd. All rights reserved.

PY - 2016/4/20

Y1 - 2016/4/20

N2 - A Nd/Na heterobimetallic complex prepared from an amide-based chiral ligand, Nd alkoxide, and NaHMDS is a highly efficient heterogeneous catalyst for an anti-selective catalytic asymmetric nitroaldol reaction. Nd alkoxide is sensitive to moisture, expensive, and scarce, making it difficult to use the Nd/Na catalyst in large-scale applications. Herein we describe a new protocol that allows for catalyst preparation from bench-stable and inexpensive NdCl3·6H2O with comparable catalytic activity.

AB - A Nd/Na heterobimetallic complex prepared from an amide-based chiral ligand, Nd alkoxide, and NaHMDS is a highly efficient heterogeneous catalyst for an anti-selective catalytic asymmetric nitroaldol reaction. Nd alkoxide is sensitive to moisture, expensive, and scarce, making it difficult to use the Nd/Na catalyst in large-scale applications. Herein we describe a new protocol that allows for catalyst preparation from bench-stable and inexpensive NdCl3·6H2O with comparable catalytic activity.

KW - Bimetallic complex

KW - Enantioselective

KW - Flow reaction

KW - Neodymium

KW - Nitroaldol

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DO - 10.1016/j.tetlet.2016.03.041

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Preparation of Nd/Na heterogeneous catalyst from bench-stable and inexpensive Nd salt for an anti-selective catalytic asymmetric nitroaldol reaction

Abstract

Keywords

ASJC Scopus subject areas

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