Ring-strain-enabled reaction discovery: new heterocycles from bicyclo[1.1.0]butanes

Accounts of Chemical Research
Maciej A A WalczakPeter Wipf

Abstract

Mechanistically as well as synthetically, bicyclo[1.1.0]butanes represent one of the most fascinating classes of organic compounds. They offer a unique blend of compact size (four carbon atoms), high reactivity (strain energy of 66 kcal/mol), and mechanistic pathway diversity that can be harvested for the rapid assembly of complex scaffolds. The C(1)-C(3) bond combines the electronic features of both σ and π bonds with facile homolytic and heterolytic bond dissociation properties and thereby readily engages pericyclic, transition-metal-mediated, nucleophilic, and electrophilic pathways as well as radical acceptor and donor substrates. Despite this multifaceted reaction profile and recent advances in the preparation of bicylo[1.1.0]butanes, the current portfolio of synthetic applications is still limited compared with those of cyclopropanes and cyclobutanes. In this Account, we describe our work over the past decade on the exploration of substituent effects on the ring strain and the reactivity of bicyclo[1.1.0]butanes, particularly in the context of metal-mediated processes. We first describe Rh(I)-catalyzed cycloisomerization reactions of N-allyl amines to give pyrrolidine and azepine heterocycles. The regioselectivity of the ...Continue Reading

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Citations

Jan 28, 2016·Science·Ryan GianatassioPhil S Baran
Aug 16, 2016·Organic Letters·John A MilliganPeter Wipf
Feb 1, 2017·Journal of the American Chemical Society·Justin M LopchukPhil S Baran
Mar 30, 2017·Journal of the American Chemical Society·Wrickban MazumdarTom G Driver
Feb 23, 2017·Chemistry : a European Journal·Lucía Álvarez-RodríguezMiguel A Sierra
Oct 21, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Zahra Alimohammadi KeyvaniMansour Zahedi
Aug 16, 2016·Chemical Communications : Chem Comm·Gen-Qiang ChenMin Shi
Jul 15, 2015·Chemical Society Reviews·Tegan P Stockdale, Craig M Williams
Mar 24, 2016·Nature Chemistry·John A Milligan, Peter Wipf
Jun 11, 2019·Organic & Biomolecular Chemistry·Riccardo Gava, Elena Fernández
Dec 12, 2019·Chemistry : a European Journal·Brett D SchwartzLara R Malins
Apr 7, 2018·Science·Kai ChenFrances H Arnold
Dec 12, 2018·Nature Chemistry·Alexander FawcettVarinder K Aggarwal
Jan 27, 2019·Nature Chemistry·Alejandro Parra, Mariola Tortosa
Apr 29, 2021·Organic & Biomolecular Chemistry·Se Hyun KimJun Hee Lee
Apr 20, 2021·Organic Letters·Michael J Kerner, Peter Wipf
May 12, 2021·Journal of the American Chemical Society·Tobias PinkertFrank Glorius
Jun 8, 2021·Chemical Science·Janis JermaksTristan H Lambert
Jul 24, 2021·Nature Chemistry·Devavrat SatheJunpeng Wang
Dec 4, 2019·Journal of the American Chemical Society·Songjie YuVarinder K Aggarwal
Aug 23, 2018·Journal of the American Chemical Society·Quan LiIvan Aprahamian
Feb 28, 2020·Journal of the American Chemical Society·Michał OciepaDorota Gryko
Jul 31, 2020·ACS Catalysis·Rudi FasanHuimin Zhao
Oct 14, 2020·Journal of the American Chemical Society·Keisuke TokunagaAkio Ojida

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