Asymmetric [4+3] cycloadditions between benzofuranyldiazoacetates and dienes: formal synthesis of (+)-frondosin B

Organic Letters
Jeremy P Olson, Huw M L Davies

Abstract

The reaction of benzofuranyldiazoacetates with 1,3-dienes catalyzed by the dirhodium tetracarboxylate Rh2(R-DOSP)4, generates formal [4+3] cycloadducts with >94% de and 91-98% ee. The reaction proceeds by a tandem cyclopropanation/Cope rearrangement followed by a stereoselective tautomerization. This methodology was extended to a formal synthesis of (+)-frondosin B.

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Citations

Aug 14, 2010·Journal of the American Chemical Society·Yajing LianHuw M L Davies
Oct 23, 2009·Chemical Society Reviews·Huw M L Davies, Justin R Denton
Sep 21, 2010·Chemical Communications : Chem Comm·Wanxiang Zhao, Junliang Zhang
Nov 9, 2010·Chemical Communications : Chem Comm·Michael Harmata
Nov 11, 2014·Organic & Biomolecular Chemistry·Ryosuke HaraguchiSeijiro Matsubara
Oct 20, 2012·Angewandte Chemie·Appaso Mahadev JadhavRai-Shung Liu
Nov 6, 2018·Chemical Society Reviews·Zengsheng YinPauline Chiu
Jul 1, 2010·Chemical Science·Maud ReiterDavid W C Macmillan
Mar 8, 2014·Beilstein Journal of Organic Chemistry·Sebastian Krüger, Tanja Gaich
Sep 29, 2011·Organic & Biomolecular Chemistry·Do W LeeWilliam A Donaldson
Nov 29, 2013·Chemistry : a European Journal·Duchan R LaplaceJohan M Winne
Mar 3, 2021·Organic & Biomolecular Chemistry·Breanna M Tomiczek, Alexander J Grenning
Jul 30, 2009·The Journal of Organic Chemistry·Jørn HansenHuw M L Davies
Oct 26, 2010·Organic Letters·Yoshiaki TakadaSeijiro Matsubara
Jul 21, 2011·Organic Letters·Hengbin WangHuw M L Davies
May 7, 2013·The Journal of Organic Chemistry·Vinayak Vishnu PagarRai-Shung Liu
Mar 1, 2014·Journal of the American Chemical Society·E Zachary OblakDennis L Wright
Mar 1, 2019·ACS Catalysis·Heiko SommerIlan Marek

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