Forging Odd-Membered Rings: Palladium-Catalyzed Asymmetric Cycloadditions of Trimethylenemethane

Accounts of Chemical Research
Barry M Trost, Guillaume Mata

Abstract

The catalytic asymmetric synthesis of complex molecules has been the focus of our research program for several decades because such strategies have significant utility for the construction of chiral building blocks for drug development as well as the total synthesis of natural products. Cycloaddition reactions are very powerful transformations in organic synthesis providing access to highly functionalized motifs from simple starting materials. In concert with this central interest, four decades ago, we reported the palladium-catalyzed trimethylenemethane (TMM) cycloaddition for forging odd-membered ring systems. In recent years, we focused our attention on the development of powerful ligand scaffolds which enable the preparation of valuable products with complete control of chemo-, regio-, diastereo-, and enantioselectivity, thereby addressing several limitations in the field of palladium-catalyzed asymmetric cycloadditions. The first section of this Account will outline the discovery of a new class of highly modular pyrrolidine-based phosphoramidite and diamidophosphite chiral ligands which facilitate [3 + 2] cycloadditions of TMM donors, opening a new area in asymmetric construction of five-membered rings.The formation of the...Continue Reading

References

Feb 1, 1996·Chemical Reviews·Mark LautensWilliam Tam
Oct 13, 2005·Journal of the American Chemical Society·Barry M TrostDiana C Dinh
Oct 13, 2006·Journal of the American Chemical Society·Barry M TrostUlrike Schwörer
Sep 25, 2007·Journal of the American Chemical Society·Barry M TrostJames P Stambuli
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Jul 18, 2009·Organic Letters·Barry M Trost, Patrick J McDougall
May 31, 2014·Journal of the American Chemical Society·Barry M TrostDustin A Bringley
Jun 6, 2014·ACS Medicinal Chemistry Letters·David Barnes-SeemanPanos Hatsis
Jul 23, 2015·Journal of Medicinal Chemistry·Eric P GillisNicholas A Meanwell
Aug 21, 2015·Journal of the American Chemical Society·Barry M Trost, Laurent Debien
Feb 6, 2020·Nature Chemistry·Barry M TrostChao-I Joey Hung

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Citations

Dec 11, 2020·Chemical Communications : Chem Comm·Batoul RkeinIsabelle Chataigner
Dec 29, 2020·Beilstein Journal of Organic Chemistry·Zhuo Wang, Junyang Liu
Dec 19, 2020·Journal of the American Chemical Society·Barry M Trost, Zhiwei Jiao
Sep 9, 2020·Journal of the American Chemical Society·Hojoon Park, Jin-Quan Yu
Oct 15, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yoshikazu Horino, Toshinobu Korenaga

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