Asymmetric catalysis via dynamic substrate/ligand/rare earth metal conglomerate

Akihiro Nojiri; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ja800326d

Asymmetric catalysis via dynamic substrate/ligand/rare earth metal conglomerate

Akihiro Nojiri, Naoya Kumagai, Masakatsu Shibasaki

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

56 Citations (Scopus)

Abstract

A highly enantio- and diastereoselective catalytic asymmetric Mannich-type reaction of α-cyanoketones and N-Boc imines promoted by an amide ligand/Sc(OⁱPr)₃ catalyst is described. The similar reaction outcome is obtained with/without precomplexation of catalyst, suggesting that reaction components in a non-ordered conglomerate mixture orchestrate to form an ordered transition state during the reaction. Spectroscopic data and Eyring plot are consistent with this assumption.

Original language	English
Pages (from-to)	5630-5631
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	17
DOIs	https://doi.org/10.1021/ja800326d
Publication status	Published - 2008 Apr 30
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "A highly enantio- and diastereoselective catalytic asymmetric Mannich-type reaction of α-cyanoketones and N-Boc imines promoted by an amide ligand/Sc(OiPr)3 catalyst is described. The similar reaction outcome is obtained with/without precomplexation of catalyst, suggesting that reaction components in a non-ordered conglomerate mixture orchestrate to form an ordered transition state during the reaction. Spectroscopic data and Eyring plot are consistent with this assumption.",

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AU - Shibasaki, Masakatsu

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N2 - A highly enantio- and diastereoselective catalytic asymmetric Mannich-type reaction of α-cyanoketones and N-Boc imines promoted by an amide ligand/Sc(OiPr)3 catalyst is described. The similar reaction outcome is obtained with/without precomplexation of catalyst, suggesting that reaction components in a non-ordered conglomerate mixture orchestrate to form an ordered transition state during the reaction. Spectroscopic data and Eyring plot are consistent with this assumption.

AB - A highly enantio- and diastereoselective catalytic asymmetric Mannich-type reaction of α-cyanoketones and N-Boc imines promoted by an amide ligand/Sc(OiPr)3 catalyst is described. The similar reaction outcome is obtained with/without precomplexation of catalyst, suggesting that reaction components in a non-ordered conglomerate mixture orchestrate to form an ordered transition state during the reaction. Spectroscopic data and Eyring plot are consistent with this assumption.

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Asymmetric catalysis via dynamic substrate/ligand/rare earth metal conglomerate

Abstract

ASJC Scopus subject areas

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