Catalytic Three-Component Synthesis of Functionalized Naphtho[2,1-b ]oxecines via a Double Bond Cleavage-Rearrangement Cascade

Organic Letters
Cheng-Long JiBo Jiang

Abstract

A new double annulation cascade involving a [2 + 2] cycloaddition-retroelectrocyclization (CA-RE) process was first reported, leading to the generation of unprecedented dibenzoannulated naphtho[2,1-b]oxecines with good to excellent yields and high stereoselectivity through catalytic scission/recombination of C-C double bonds under the mild conditions. An Y(OTf)3-catalyzed three-component reaction of α-alkynyl naphthalen-2-ols with β,γ-unsaturated α-ketoesters enabled direct ring expansion of the naphthalene ring and carbon-carbon double bond cleavage/rearrangement of α-ketoesters to give macrocyclic architectures.

References

Jun 26, 2001·The Journal of Organic Chemistry·X BaucherelS Jugé
Apr 11, 2002·Journal of the American Chemical Society·Benjamin R TravisBabak Borhan
Dec 14, 2004·Chemical Society Reviews·Chul-Ho Jun
Feb 14, 2006·Organic Letters·Dong XingZhangjie Shi
Feb 21, 2007·Journal of the American Chemical Society·Kazunori MiyamotoMasahito Ochiai
Nov 13, 2007·Nature·Amir H Hoveyda, Adil R Zhugralin
Dec 17, 2009·Chemical Reviews·Georgios C Vougioukalakis, Robert H Grubbs
Mar 12, 2010·Chemical Communications : Chem Comm·Shin-ichiro Kato, François Diederich
Nov 18, 2010·Organic Letters·Prem P Thottumkara, Thottumkara K Vinod
Jul 30, 2011·Chemical Communications : Chem Comm·Masakazu MorimotoTsuyoshi Michinobu
Sep 10, 2011·Organic Letters·Songlin NiuRaymond Ziessel
Nov 8, 2012·The Journal of Organic Chemistry·Raúl GarcíaNazario Martín
Aug 2, 2013·Journal of the American Chemical Society·Teng Wang, Ning Jiao
Nov 27, 2014·Angewandte Chemie·Melanie ChiuFrançois Diederich
Jul 1, 2016·Chemistry : a European Journal·Johan BidangeChristian Bruneau
Sep 15, 2016·The Journal of Organic Chemistry·Tian-Shu ZhangBo Jiang
Mar 23, 2018·The Journal of Organic Chemistry·Hyunseok KimPhil Ho Lee
May 22, 2018·Journal of the American Chemical Society·Shiqi JiaHailong Yan
Nov 23, 2018·Journal of the American Chemical Society·Yu TanHailong Yan

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