Iridium-catalyzed enantioselective cycloisomerization of nitrogen-bridged 1,6-enynes to 3-azabicylo[4.1.0]heptenes

Takanori Shibata; Yuka Kobayashi; Shunsuke Maekawa; Natsuko Toshida; Kentaro Takagi

doi:10.1016/j.tet.2005.07.039

Iridium-catalyzed enantioselective cycloisomerization of nitrogen-bridged 1,6-enynes to 3-azabicylo[4.1.0]heptenes

Takanori Shibata^*, Yuka Kobayashi, Shunsuke Maekawa, Natsuko Toshida, Kentaro Takagi

^*Corresponding author for this work

School of Advanced Science and Engineering

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

80 Citations (Scopus)

Abstract

A cationic iridium complex catalyzes a cycloisomerization of nitrogen-bridged 1,6-enynes to give 3-azabicyclo[4.1.0]heptenes in good to high yield. When an iridium-chiral diphosphine complex is used, the reaction proceeds enantiomerically to give chiral cyclopropanes fused by a six-membered ring system.

Original language	English
Pages (from-to)	9018-9024
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2005.07.039
Publication status	Published - 2005 Sept 19

Keywords

Cycloisomerization
Cyclopropanes
Enantioselective
Enynes
Iridium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.07.039

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title = "Iridium-catalyzed enantioselective cycloisomerization of nitrogen-bridged 1,6-enynes to 3-azabicylo[4.1.0]heptenes",

abstract = "A cationic iridium complex catalyzes a cycloisomerization of nitrogen-bridged 1,6-enynes to give 3-azabicyclo[4.1.0]heptenes in good to high yield. When an iridium-chiral diphosphine complex is used, the reaction proceeds enantiomerically to give chiral cyclopropanes fused by a six-membered ring system.",

keywords = "Cycloisomerization, Cyclopropanes, Enantioselective, Enynes, Iridium",

author = "Takanori Shibata and Yuka Kobayashi and Shunsuke Maekawa and Natsuko Toshida and Kentaro Takagi",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2005",

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T1 - Iridium-catalyzed enantioselective cycloisomerization of nitrogen-bridged 1,6-enynes to 3-azabicylo[4.1.0]heptenes

AU - Shibata, Takanori

AU - Kobayashi, Yuka

AU - Maekawa, Shunsuke

AU - Toshida, Natsuko

AU - Takagi, Kentaro

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2005/9/19

Y1 - 2005/9/19

N2 - A cationic iridium complex catalyzes a cycloisomerization of nitrogen-bridged 1,6-enynes to give 3-azabicyclo[4.1.0]heptenes in good to high yield. When an iridium-chiral diphosphine complex is used, the reaction proceeds enantiomerically to give chiral cyclopropanes fused by a six-membered ring system.

AB - A cationic iridium complex catalyzes a cycloisomerization of nitrogen-bridged 1,6-enynes to give 3-azabicyclo[4.1.0]heptenes in good to high yield. When an iridium-chiral diphosphine complex is used, the reaction proceeds enantiomerically to give chiral cyclopropanes fused by a six-membered ring system.

KW - Cycloisomerization

KW - Cyclopropanes

KW - Enantioselective

KW - Enynes

KW - Iridium

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U2 - 10.1016/j.tet.2005.07.039

DO - 10.1016/j.tet.2005.07.039

M3 - Article

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SN - 0040-4020

VL - 61

SP - 9018

EP - 9024

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Iridium-catalyzed enantioselective cycloisomerization of nitrogen-bridged 1,6-enynes to 3-azabicylo[4.1.0]heptenes

Abstract

Keywords

ASJC Scopus subject areas

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