The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst

Toshio Shinohara; Midori A. Arai; Kazuhiko Wakita; Takayoshi Arai; Hiroaki Sasai

doi:10.1016/S0040-4039(02)02650-3

The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst

Toshio Shinohara, Midori A. Arai, Kazuhiko Wakita, Takayoshi Arai, Hiroaki Sasai

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

12 Citations (Scopus)

Abstract

The highly ligand acceleration effect of spiro bis(isoxazoline) ligand (SPRIX) on the Pd(II)-catalyzed intramolecular aminocarbonylation of alkenyl amine derivatives was realized. Furthermore, the chiral Pd(II)-SPRIX catalyst accomplished the first enantioselective intramolecular aminocarbonylation. The reaction of N-(2,2-dimethyl-pent-4-enyl)-p-toluenesulfonamide in the presence of Pd(II)-SPRIX catalyst and p-benzoquinone in methanol under a carbon monoxide atmosphere afforded [4,4-dimethyl-1-(p-toluene-sulfonyl)-pyrrolidin-2-yl]-acetic acid methyl ester in good yield with moderate enantioselectivity.

Original language	English
Pages (from-to)	711-714
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4039(02)02650-3
Publication status	Published - 2003 Jan 20
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst",

abstract = "The highly ligand acceleration effect of spiro bis(isoxazoline) ligand (SPRIX) on the Pd(II)-catalyzed intramolecular aminocarbonylation of alkenyl amine derivatives was realized. Furthermore, the chiral Pd(II)-SPRIX catalyst accomplished the first enantioselective intramolecular aminocarbonylation. The reaction of N-(2,2-dimethyl-pent-4-enyl)-p-toluenesulfonamide in the presence of Pd(II)-SPRIX catalyst and p-benzoquinone in methanol under a carbon monoxide atmosphere afforded [4,4-dimethyl-1-(p-toluene-sulfonyl)-pyrrolidin-2-yl]-acetic acid methyl ester in good yield with moderate enantioselectivity.",

author = "Toshio Shinohara and Arai, {Midori A.} and Kazuhiko Wakita and Takayoshi Arai and Hiroaki Sasai",

note = "Funding Information: This work was supported by the Ministry of Education, Culture, Sports, Science and Technology, Japan. T.S. and M.A.A. appreciate Research Fellowships from the Japan Society for the Promotion of Science (JSPS) for Young Scientists. We also thank the technical staff at the Materials Analysis Center of ISIR.",

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doi = "10.1016/S0040-4039(02)02650-3",

language = "English",

volume = "44",

pages = "711--714",

journal = "Tetrahedron Letters",

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T1 - The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst

AU - Shinohara, Toshio

AU - Arai, Midori A.

AU - Wakita, Kazuhiko

AU - Arai, Takayoshi

AU - Sasai, Hiroaki

N1 - Funding Information: This work was supported by the Ministry of Education, Culture, Sports, Science and Technology, Japan. T.S. and M.A.A. appreciate Research Fellowships from the Japan Society for the Promotion of Science (JSPS) for Young Scientists. We also thank the technical staff at the Materials Analysis Center of ISIR.

PY - 2003/1/20

Y1 - 2003/1/20

N2 - The highly ligand acceleration effect of spiro bis(isoxazoline) ligand (SPRIX) on the Pd(II)-catalyzed intramolecular aminocarbonylation of alkenyl amine derivatives was realized. Furthermore, the chiral Pd(II)-SPRIX catalyst accomplished the first enantioselective intramolecular aminocarbonylation. The reaction of N-(2,2-dimethyl-pent-4-enyl)-p-toluenesulfonamide in the presence of Pd(II)-SPRIX catalyst and p-benzoquinone in methanol under a carbon monoxide atmosphere afforded [4,4-dimethyl-1-(p-toluene-sulfonyl)-pyrrolidin-2-yl]-acetic acid methyl ester in good yield with moderate enantioselectivity.

AB - The highly ligand acceleration effect of spiro bis(isoxazoline) ligand (SPRIX) on the Pd(II)-catalyzed intramolecular aminocarbonylation of alkenyl amine derivatives was realized. Furthermore, the chiral Pd(II)-SPRIX catalyst accomplished the first enantioselective intramolecular aminocarbonylation. The reaction of N-(2,2-dimethyl-pent-4-enyl)-p-toluenesulfonamide in the presence of Pd(II)-SPRIX catalyst and p-benzoquinone in methanol under a carbon monoxide atmosphere afforded [4,4-dimethyl-1-(p-toluene-sulfonyl)-pyrrolidin-2-yl]-acetic acid methyl ester in good yield with moderate enantioselectivity.

UR - http://www.scopus.com/inward/record.url?scp=0037454989&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037454989&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)02650-3

DO - 10.1016/S0040-4039(02)02650-3

M3 - Article

AN - SCOPUS:0037454989

SN - 0040-4039

VL - 44

SP - 711

EP - 714

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst

Abstract

ASJC Scopus subject areas

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