Desymmetrization of prochiral methylenes by asymmetric chain-walking cyclization using bioxazoline palladium catalysts

Masayuki Shigekane; Tomonori Arai; Makoto Tamura; Tatsuya Uchida; Fumitoshi Kakiuchi; Takuya Kochi

doi:10.1016/j.tetlet.2022.154292

Desymmetrization of prochiral methylenes by asymmetric chain-walking cyclization using bioxazoline palladium catalysts

Masayuki Shigekane, Tomonori Arai, Makoto Tamura, Tatsuya Uchida, Fumitoshi Kakiuchi, Takuya Kochi

Department of Chemistry

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

Abstract

We present here that the use of bioxazoline ligands improved the enantioselectivity of the palladium-catalyzed chain-walking cycloisomerization of 1,n-dienes. The new system was applied to the asymmetric chain-walking cycloisomerization of a variety of 1,n-dienes as well as asymmetric hydrosilylation/cyclization of a 1,8-diene.

Original language	English
Article number	154292
Journal	Tetrahedron Letters
Volume	114
DOIs	https://doi.org/10.1016/j.tetlet.2022.154292
Publication status	Published - 2023 Jan 12

Keywords

Asymmetric cycloisomerization
Bioxazoline ligands
Chain walking
Palladium catalysts
Remote Functionalization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2022.154292

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title = "Desymmetrization of prochiral methylenes by asymmetric chain-walking cyclization using bioxazoline palladium catalysts",

abstract = "We present here that the use of bioxazoline ligands improved the enantioselectivity of the palladium-catalyzed chain-walking cycloisomerization of 1,n-dienes. The new system was applied to the asymmetric chain-walking cycloisomerization of a variety of 1,n-dienes as well as asymmetric hydrosilylation/cyclization of a 1,8-diene.",

keywords = "Asymmetric cycloisomerization, Bioxazoline ligands, Chain walking, Palladium catalysts, Remote Functionalization",

author = "Masayuki Shigekane and Tomonori Arai and Makoto Tamura and Tatsuya Uchida and Fumitoshi Kakiuchi and Takuya Kochi",

note = "Funding Information: This work was supported, in part, by JSPS KAKENHI Grant Numbers 22H02085 (Grant-in-Aid for Scientific Research (B)), 18H01985 (Grant-in-Aid for Scientific Research (B)), and 18H04271 (Precisely Designed Catalysts with Customized Scaffolding). Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

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doi = "10.1016/j.tetlet.2022.154292",

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T1 - Desymmetrization of prochiral methylenes by asymmetric chain-walking cyclization using bioxazoline palladium catalysts

AU - Shigekane, Masayuki

AU - Arai, Tomonori

AU - Tamura, Makoto

AU - Uchida, Tatsuya

AU - Kakiuchi, Fumitoshi

AU - Kochi, Takuya

N1 - Funding Information: This work was supported, in part, by JSPS KAKENHI Grant Numbers 22H02085 (Grant-in-Aid for Scientific Research (B)), 18H01985 (Grant-in-Aid for Scientific Research (B)), and 18H04271 (Precisely Designed Catalysts with Customized Scaffolding). Publisher Copyright: © 2022 Elsevier Ltd

PY - 2023/1/12

Y1 - 2023/1/12

N2 - We present here that the use of bioxazoline ligands improved the enantioselectivity of the palladium-catalyzed chain-walking cycloisomerization of 1,n-dienes. The new system was applied to the asymmetric chain-walking cycloisomerization of a variety of 1,n-dienes as well as asymmetric hydrosilylation/cyclization of a 1,8-diene.

AB - We present here that the use of bioxazoline ligands improved the enantioselectivity of the palladium-catalyzed chain-walking cycloisomerization of 1,n-dienes. The new system was applied to the asymmetric chain-walking cycloisomerization of a variety of 1,n-dienes as well as asymmetric hydrosilylation/cyclization of a 1,8-diene.

KW - Asymmetric cycloisomerization

KW - Bioxazoline ligands

KW - Chain walking

KW - Palladium catalysts

KW - Remote Functionalization

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DO - 10.1016/j.tetlet.2022.154292

M3 - Article

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VL - 114

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

M1 - 154292

ER -

Desymmetrization of prochiral methylenes by asymmetric chain-walking cyclization using bioxazoline palladium catalysts

Abstract

Keywords

ASJC Scopus subject areas

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