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

研究成果: 雜誌貢獻期刊論文同行評審

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
40
發行號20
DOIs
出版狀態已發佈 - 2021 十月 25

ASJC Scopus subject areas

  • 物理與理論化學
  • 有機化學
  • 無機化學

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