Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes

Yukimasa Aida; Haruki Sugiyama; Hidehiro Uekusa; Yu Shibata; Ken Tanaka

doi:10.1021/acs.orglett.6b01116

Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes

Yukimasa Aida, Haruki Sugiyama, Hidehiro Uekusa, Yu Shibata, Ken Tanaka

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

18 Citations (Scopus)

Abstract

It has been established that a cationic rhodium(I)/axially chiral biaryl bisphosphine complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of α,ω-diynes with electron-rich and unstrained unsymmetrical 1,2-disubstituted alkenes to give chiral multicyclic compounds with good yields and ee values. Interestingly, enantioselectivity highly depends on the structures of α,ω-diynes used presumably due to the presence of two distinct reaction pathways.

Original language	English
Pages (from-to)	2672-2675
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.6b01116
Publication status	Published - 2016 Jun 3
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "It has been established that a cationic rhodium(I)/axially chiral biaryl bisphosphine complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of α,ω-diynes with electron-rich and unstrained unsymmetrical 1,2-disubstituted alkenes to give chiral multicyclic compounds with good yields and ee values. Interestingly, enantioselectivity highly depends on the structures of α,ω-diynes used presumably due to the presence of two distinct reaction pathways.",

author = "Yukimasa Aida and Haruki Sugiyama and Hidehiro Uekusa and Yu Shibata and Ken Tanaka",

note = "Funding Information: This work was supported in part by the ACT-C from JST (Japan) and Grants-in-Aids for Scientific Research (Nos. 15H03775 and 26102004) from MEXT (Japan). We thank Takasago International Corp. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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T1 - Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes

AU - Aida, Yukimasa

AU - Sugiyama, Haruki

AU - Uekusa, Hidehiro

AU - Shibata, Yu

AU - Tanaka, Ken

N1 - Funding Information: This work was supported in part by the ACT-C from JST (Japan) and Grants-in-Aids for Scientific Research (Nos. 15H03775 and 26102004) from MEXT (Japan). We thank Takasago International Corp. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/6/3

Y1 - 2016/6/3

N2 - It has been established that a cationic rhodium(I)/axially chiral biaryl bisphosphine complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of α,ω-diynes with electron-rich and unstrained unsymmetrical 1,2-disubstituted alkenes to give chiral multicyclic compounds with good yields and ee values. Interestingly, enantioselectivity highly depends on the structures of α,ω-diynes used presumably due to the presence of two distinct reaction pathways.

AB - It has been established that a cationic rhodium(I)/axially chiral biaryl bisphosphine complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of α,ω-diynes with electron-rich and unstrained unsymmetrical 1,2-disubstituted alkenes to give chiral multicyclic compounds with good yields and ee values. Interestingly, enantioselectivity highly depends on the structures of α,ω-diynes used presumably due to the presence of two distinct reaction pathways.

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Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes

Abstract

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