Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles.

Beilstein Journal of Organic Chemistry
Dingqiao YangXiongjun Zuo

Abstract

Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography.

References

Mar 17, 1995·Journal of Medicinal Chemistry·R PerroneS Govoni
May 25, 2002·Organic Letters·Mark LautensGiliane Bouchain
Jul 18, 2002·Chemical Communications : Chem Comm·Masahiro Murakami, Hideyuki Igawa
Aug 3, 2002·Organic Letters·Craig G BatesD Venkataraman
Jan 22, 2003·Accounts of Chemical Research·Mark LautensSheldon Hiebert
Apr 12, 2003·Organic Letters·Ramón Gómez ArrayásJuan C Carretero
Apr 3, 2004·The Journal of Organic Chemistry·Paul Leong, Mark Lautens
Apr 29, 2004·Angewandte Chemie·Karine Tissot-CrosetAlexandre Alexakis
Sep 25, 2004·Organic Letters·Chi-Li Chen, Stephen F Martin
Oct 8, 2004·Journal of the American Chemical Society·Fernando LópezBen L Feringa
Feb 24, 2006·Chemical Communications : Chem Comm·Fernando LópezBen L Feringa
Aug 5, 2006·Angewandte Chemie·Caroline A FalciolaAlexandre Alexakis
Jan 15, 2009·Journal of the American Chemical Society·Robert WebsterMark Lautens

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Citations

Nov 6, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Huayi SuoJianquan Kan
Dec 4, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wen YangDingqiao Yang
Sep 17, 2013·Chemical Communications : Chem Comm·Renshi LuoAlbert S C Chan
Feb 20, 2014·Organic & Biomolecular Chemistry·Dingqiao Yang, Ni Liang
Feb 6, 2021·Chemical Society Reviews·Sundaravel Vivek KumarPatrick J Guiry

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Methods Mentioned

BETA
gel column chromatography
X-ray
column chromatography

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