Design and synthesis of chiral hybrid spiro (isoxazole–isoxazoline) ligands

Koranne, Priti S.; Tsujihara, Tetsuya; Arai, Midori A.; Bajracharya, Gan B.; Suzuki, Takayoshi; Onitsuka, Kiyotaka; Sasai, Hiroaki

doi:10.1016/j.tetasy.2007.04.010

Cited by 28 publications

(11 citation statements)

References 34 publications

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“…8 Asymmetric synthesis of SPRIX 2 has been achieved by using an optically pure starting material. 9,10 Spiro bis(isoxazole) ligands (3) 11 and spiro (isoxazoleisoxazoline) hybrid ligands (4) 12,13 have also been prepared.…”

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confidence: 99%

Structural Features and Asymmetric Environment of i‐Pr‐SPRIX Ligand

et al. 2015

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Novel chiral diisopropyl spiro bis(isoxazoline) ligands, anti-i-Pr-SPRIX and syn-i-Pr-SPRIX, were designed and synthesized. Their catalytic utility, X-ray crystallographic analyses, and complexation studies demonstrated the structural features of tetraisopropyl spiro bis(isoxazoline) ligand, i-Pr-SPRIX, which is a prominent ligand in various enantioselective Pd catalytic processes: All i-Pr groups work in collaboration to create an effective asymmetric environment.

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confidence: 99%

Structural Features and Asymmetric Environment of i‐Pr‐SPRIX Ligand

et al. 2015

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“…The enantioselective synthesis of 3 aa was examined by using several chiral ligands, and up to 39% enantioselectivity was obtained (Scheme 5) by using the isoxazoline-isoxazole hybrid ligand [23] (for more details, see SI).…”

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confidence: 99%

Synthesis of Allylamine Derivatives via Intermolecular Aza‐Wacker‐Type Reaction Promoted by Palladium‐SPRIX Catalyst

et al. 2020

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An intermolecular aza‐Wacker‐type reaction was developed. When a readily available olefin was treated with a nitrogen nucleophile in the presence of a Pd‐SPRIX complex and potassium persulfate, allylamine derivatives were obtained with high yield and excellent regioselectivity. The mechanistic studies showed that the reaction followed first‐order dependence on the olefin as well as palladium catalyst, but zero‐order dependence on the nitrogen nucleophile.

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“…Thus we designed a new hybrid spiro isoxazolineisoxazole ligand containing an unsymmetrical spiro backbone. 27 It was anticipated that in this new design of hybrid ligand, only two diastereomers would be formed and this is advantageous, since in the case of synthesis of SPRIX, three diastereomers were obtained. A computational calculation study of possible diastereomers with varying ring size such as spiro [4.4]nonane, spiro [4.5]decane, spiro [5.5]undecane and spiro [4.6]undecane using HF/6-31G* revealed that spiro [4.5]decane skeleton has the most suitable design.…”

Section: Scheme 12: Pd-catalyzed Tandem Cyclization Of the Dialkenyl mentioning

confidence: 99%