Enantioselective Dirhodium(II)-Catalyzed Cyclopropanations with Trimethylsilylethyl and Trichloroethyl Aryldiazoacetates

Tetrahedron
Solymar NegrettiH M Davies

Abstract

Highly functionalized cyclopropanecarboxylates were readily prepared by rhodium-catalyzed cyclopropanation of alkenes with aryldiazoacetates and styryldiazoaceates, in which the ester functionality is either trimethylsilylethyl (TMSE) or trichlorethyl (TCE). By having labile protecting groups on the ester, chiral triarylcyclopropane carboxylate ligands were conveniently prepared. The asymmetric induction during cyclopropanation is dependent on the nature of the ester group and the chiral dirhodium tetracarboxylate catalyst. The prolinate catalyst Rh2(S-DOSP)4 was the optimum catalyst for asymmetric intermolecular cyclopropanation of TMSE diazoesters with styrene, while Rh2(R-BPCP)4 was the optimum catalyst for TCE diazoesters.

References

Oct 2, 2001·The Journal of Organic Chemistry·H M Davies, R J Townsend
Apr 10, 2003·Chemical Reviews·Hélène LebelAndré B Charette
Apr 26, 2003·Organic Letters·Huw M L Davies, Chandrasekar Venkataramani
Aug 14, 2003·Chemical Reviews·Huw M L Davies, Rohan E J Beckwith
Dec 18, 2003·Journal of the American Chemical Society·Daniel T NowlanDaniel A Singleton
Jul 30, 2009·The Journal of Organic Chemistry·Jørn HansenHuw M L Davies
Jul 20, 2011·Organic Letters·Stephanie R OvallesHuw M L Davies
May 18, 2012·Chemical Society Reviews·David Y-K ChenJean-Alexandre Richard
Jan 5, 2013·Organic Letters·Changming Qin, Huw M L Davies
Sep 13, 2013·Journal of the American Chemical Society·Changming Qin, Huw M L Davies
Sep 21, 2013·Chemical Science·Hengbin WangHuw M L Davies
Nov 29, 2013·Organic Letters·David M GuptillHuw M L Davies
Jun 17, 2014·Journal of the American Chemical Society·Changming Qin, Huw M L Davies
Dec 5, 2014·Journal of the American Chemical Society·David M Guptill, Huw M L Davies

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Citations

Mar 15, 2018·Angewandte Chemie·Takayuki NakamuroMasahiro Murakami
Jan 8, 2020·Angewandte Chemie·Bowen Zhang, Huw M L Davies
Jan 18, 2017·Chemistry : a European Journal·Liangbing FuHuw M L Davies
Feb 26, 2016·Journal of the American Chemical Society·Christophe WerléAlois Fürstner
Apr 19, 2019·Journal of the American Chemical Society·Erik J T Phipps, Tomislav Rovis

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