Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands

Midori A. Arai; Takayoshi Arai; Hiroaki Sasai

doi:10.1021/ol9902881

Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands

Midori A. Arai, Takayoshi Arai, Hiroaki Sasai

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

96 Citations (Scopus)

Abstract

(formula presented) A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition. The optically pure SPRIX greatly accelerated the Cu(acac)₂-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal-catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.

Original language	English
Pages (from-to)	1795-1797
Number of pages	3
Journal	Organic Letters
Volume	1
Issue number	11
DOIs	https://doi.org/10.1021/ol9902881
Publication status	Published - 1999 Dec 2
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(formula presented) A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition. The optically pure SPRIX greatly accelerated the Cu(acac)2-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal-catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.",

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T1 - Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands

AU - Arai, Midori A.

AU - Arai, Takayoshi

AU - Sasai, Hiroaki

PY - 1999/12/2

Y1 - 1999/12/2

N2 - (formula presented) A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition. The optically pure SPRIX greatly accelerated the Cu(acac)2-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal-catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.

AB - (formula presented) A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition. The optically pure SPRIX greatly accelerated the Cu(acac)2-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal-catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.

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