Cross-Dimerization of 2,5-Dihydrofuran with Conjugated Dienes Catalyzed by (Chiral Diene)ruthenium(0) Complexes and Origins of the Enantioselectivity

Masafumi Hirano; Shuhei Machida; Ryota Abe; Takuya Mishina; Nobuyuki Komine; Hsyueh Liang Wu

doi:10.1021/acs.organomet.1c00368

Cross-Dimerization of 2,5-Dihydrofuran with Conjugated Dienes Catalyzed by (Chiral Diene)ruthenium(0) Complexes and Origins of the Enantioselectivity

Masafumi Hirano^*, Shuhei Machida, Ryota Abe, Takuya Mishina, Nobuyuki Komine, Hsyueh Liang Wu

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

4 引文斯高帕斯（Scopus）

摘要

A new chiral diene complex of Ru(0), [Ru(6-naphthalene){ 4-(1S,4S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene}] (2a), catalyzes cross-dimerizations of 2,5-dihydrofuran with conjugated dienes. Treatment of 2,5-dihydrofuran (4a) with 2-phenylbutadiene (5f) catalyzed by 2a (5 mol %) at 30 °C in acetone produces the cross-dimers (E)-3-(3-phenylbut-2-en-1-yl)-2,3-dihydrofuran (6af) and (E)-3-(2-phenylbut-2-en-1-yl)-2,3-dihydrofuran (9af) in 89% yield (6af/9af = 41/48) with high enantioselectivity (91% ee for 9af). The absolute configuration of 9af is determined to be R by single-crystal X-ray spectroscopy. A series of enantioselective cross-dimerizations of 2,5-dihydrofuran with conjugated dienes are assessed for the mechanistic insight into the enantioselective cross-dimerization.

原文	英語
頁（從 - 到）	3370-3388
頁數	19
期刊	Organometallics
卷	40
發行號	20
DOIs	https://doi.org/10.1021/acs.organomet.1c00368
出版狀態	已發佈 - 2021 10月 25

ASJC Scopus subject areas

物理與理論化學
有機化學
無機化學

存取文件

10.1021/acs.organomet.1c00368

其它文件與鏈接

Link to publication in Scopus

CCDC 2071994: Experimental Crystal Structure Determination
Hirano, M. (Contributor), Machida, S. (Contributor), Abe, R. (Contributor), Mishina, T. (Contributor), Komine, N. (Contributor) & Wu, H.-L. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc27k2jf, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27k2jf&sid=DataCite
資料集: Dataset
CCDC 2071997: Experimental Crystal Structure Determination
Hirano, M. (Contributor), Machida, S. (Contributor), Abe, R. (Contributor), Mishina, T. (Contributor), Komine, N. (Contributor) & Wu, H.-L. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc27k2mj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27k2mj&sid=DataCite
資料集: Dataset
CCDC 2071998: Experimental Crystal Structure Determination
Hirano, M. (Contributor), Machida, S. (Contributor), Abe, R. (Contributor), Mishina, T. (Contributor), Komine, N. (Contributor) & Wu, H.-L. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc27k2nk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27k2nk&sid=DataCite
資料集: Dataset

引用此

@article{f6d690026ab4441092512c9519191d32,

title = "Cross-Dimerization of 2,5-Dihydrofuran with Conjugated Dienes Catalyzed by (Chiral Diene)ruthenium(0) Complexes and Origins of the Enantioselectivity",

abstract = "A new chiral diene complex of Ru(0), [Ru(6-naphthalene){ 4-(1S,4S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene}] (2a), catalyzes cross-dimerizations of 2,5-dihydrofuran with conjugated dienes. Treatment of 2,5-dihydrofuran (4a) with 2-phenylbutadiene (5f) catalyzed by 2a (5 mol %) at 30 °C in acetone produces the cross-dimers (E)-3-(3-phenylbut-2-en-1-yl)-2,3-dihydrofuran (6af) and (E)-3-(2-phenylbut-2-en-1-yl)-2,3-dihydrofuran (9af) in 89% yield (6af/9af = 41/48) with high enantioselectivity (91% ee for 9af). The absolute configuration of 9af is determined to be R by single-crystal X-ray spectroscopy. A series of enantioselective cross-dimerizations of 2,5-dihydrofuran with conjugated dienes are assessed for the mechanistic insight into the enantioselective cross-dimerization.",

author = "Masafumi Hirano and Shuhei Machida and Ryota Abe and Takuya Mishina and Nobuyuki Komine and Wu, {Hsyueh Liang}",

note = "Publisher Copyright: {\textcopyright} ",

year = "2021",

month = oct,

day = "25",

doi = "10.1021/acs.organomet.1c00368",

language = "English",

volume = "40",

pages = "3370--3388",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Cross-Dimerization of 2,5-Dihydrofuran with Conjugated Dienes Catalyzed by (Chiral Diene)ruthenium(0) Complexes and Origins of the Enantioselectivity

AU - Hirano, Masafumi

AU - Machida, Shuhei

AU - Abe, Ryota

AU - Mishina, Takuya

AU - Komine, Nobuyuki

AU - Wu, Hsyueh Liang

PY - 2021/10/25

Y1 - 2021/10/25

N2 - A new chiral diene complex of Ru(0), [Ru(6-naphthalene){ 4-(1S,4S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene}] (2a), catalyzes cross-dimerizations of 2,5-dihydrofuran with conjugated dienes. Treatment of 2,5-dihydrofuran (4a) with 2-phenylbutadiene (5f) catalyzed by 2a (5 mol %) at 30 °C in acetone produces the cross-dimers (E)-3-(3-phenylbut-2-en-1-yl)-2,3-dihydrofuran (6af) and (E)-3-(2-phenylbut-2-en-1-yl)-2,3-dihydrofuran (9af) in 89% yield (6af/9af = 41/48) with high enantioselectivity (91% ee for 9af). The absolute configuration of 9af is determined to be R by single-crystal X-ray spectroscopy. A series of enantioselective cross-dimerizations of 2,5-dihydrofuran with conjugated dienes are assessed for the mechanistic insight into the enantioselective cross-dimerization.

AB - A new chiral diene complex of Ru(0), [Ru(6-naphthalene){ 4-(1S,4S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene}] (2a), catalyzes cross-dimerizations of 2,5-dihydrofuran with conjugated dienes. Treatment of 2,5-dihydrofuran (4a) with 2-phenylbutadiene (5f) catalyzed by 2a (5 mol %) at 30 °C in acetone produces the cross-dimers (E)-3-(3-phenylbut-2-en-1-yl)-2,3-dihydrofuran (6af) and (E)-3-(2-phenylbut-2-en-1-yl)-2,3-dihydrofuran (9af) in 89% yield (6af/9af = 41/48) with high enantioselectivity (91% ee for 9af). The absolute configuration of 9af is determined to be R by single-crystal X-ray spectroscopy. A series of enantioselective cross-dimerizations of 2,5-dihydrofuran with conjugated dienes are assessed for the mechanistic insight into the enantioselective cross-dimerization.

UR - http://www.scopus.com/inward/record.url?scp=85113393893&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85113393893&partnerID=8YFLogxK

U2 - 10.1021/acs.organomet.1c00368

DO - 10.1021/acs.organomet.1c00368

M3 - Article

AN - SCOPUS:85113393893

SN - 0276-7333

VL - 40

SP - 3370

EP - 3388

JO - Organometallics

JF - Organometallics

IS - 20

ER -

Cross-Dimerization of 2,5-Dihydrofuran with Conjugated Dienes Catalyzed by (Chiral Diene)ruthenium(0) Complexes and Origins of the Enantioselectivity

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 2071994: Experimental Crystal Structure Determination

CCDC 2071997: Experimental Crystal Structure Determination

CCDC 2071998: Experimental Crystal Structure Determination

引用此