Rhodium-catalyzed enantioselective [2+2+2] cycloaddition of diynes with unfunctionalized alkenes

Takanori Shibata; Ai Kawachi; Mika Ogawa; Yusuke Kuwata; Kyoji Tsuchikama; Kohei Endo

doi:10.1016/j.tet.2007.10.053

Rhodium-catalyzed enantioselective [2+2+2] cycloaddition of diynes with unfunctionalized alkenes

Takanori Shibata^*, Ai Kawachi, Mika Ogawa, Yusuke Kuwata, Kyoji Tsuchikama, Kohei Endo

^*Corresponding author for this work

School of Advanced Science and Engineering

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

38 Citations (Scopus)

Abstract

A chiral rhodium complex catalyzed an enantioselective [2+2+2] cycloaddition of unsymmetrical diynes with norbornene, and tetracyclic products were obtained in good to excellent ee. The cycloaddition of a symmetrical diyne with styrene derivatives as coupling partners gave bicyclic products in good ee.

Original language	English
Pages (from-to)	12853-12859
Number of pages	7
Journal	Tetrahedron
Volume	63
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2007.10.053
Publication status	Published - 2007 Dec 24

Keywords

Cycloaddition
Enantioselective
Norbornene
Rhodium
Styrene

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.10.053

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title = "Rhodium-catalyzed enantioselective [2+2+2] cycloaddition of diynes with unfunctionalized alkenes",

abstract = "A chiral rhodium complex catalyzed an enantioselective [2+2+2] cycloaddition of unsymmetrical diynes with norbornene, and tetracyclic products were obtained in good to excellent ee. The cycloaddition of a symmetrical diyne with styrene derivatives as coupling partners gave bicyclic products in good ee.",

keywords = "Cycloaddition, Enantioselective, Norbornene, Rhodium, Styrene",

author = "Takanori Shibata and Ai Kawachi and Mika Ogawa and Yusuke Kuwata and Kyoji Tsuchikama and Kohei Endo",

note = "Funding Information: We thank Takasago International Corp. for the gift of SEGPHOS. This research was supported by Tokyo Ohka Foundation for The Promotion of Science and Technology and a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

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doi = "10.1016/j.tet.2007.10.053",

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T1 - Rhodium-catalyzed enantioselective [2+2+2] cycloaddition of diynes with unfunctionalized alkenes

AU - Shibata, Takanori

AU - Kawachi, Ai

AU - Ogawa, Mika

AU - Kuwata, Yusuke

AU - Tsuchikama, Kyoji

AU - Endo, Kohei

N1 - Funding Information: We thank Takasago International Corp. for the gift of SEGPHOS. This research was supported by Tokyo Ohka Foundation for The Promotion of Science and Technology and a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2007/12/24

Y1 - 2007/12/24

N2 - A chiral rhodium complex catalyzed an enantioselective [2+2+2] cycloaddition of unsymmetrical diynes with norbornene, and tetracyclic products were obtained in good to excellent ee. The cycloaddition of a symmetrical diyne with styrene derivatives as coupling partners gave bicyclic products in good ee.

AB - A chiral rhodium complex catalyzed an enantioselective [2+2+2] cycloaddition of unsymmetrical diynes with norbornene, and tetracyclic products were obtained in good to excellent ee. The cycloaddition of a symmetrical diyne with styrene derivatives as coupling partners gave bicyclic products in good ee.

KW - Cycloaddition

KW - Enantioselective

KW - Norbornene

KW - Rhodium

KW - Styrene

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DO - 10.1016/j.tet.2007.10.053

M3 - Article

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SN - 0040-4020

VL - 63

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EP - 12859

JO - Tetrahedron

JF - Tetrahedron

IS - 52

ER -

Rhodium-catalyzed enantioselective [2+2+2] cycloaddition of diynes with unfunctionalized alkenes

Abstract

Keywords

ASJC Scopus subject areas

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