Effect of ligand structure on the asymmetric cyclization of achiral olefinic organolithiums

The Journal of Organic Chemistry
Michael J MealyMichael Bech Sommer

Abstract

The ability of a large and chemically diverse set of 30 chiral ligands to effect asymmetric cyclization of 2-(N,N-diallylamino)phenyllithium (1), derived from N,N-diallyl-2-bromoaniline (2) by low-temperature lithium-bromine exchange, has been investigated in an attempt to elucidate the structural motifs required to provide high enantiofacial selectivity in the ring closure. Although none of the ligands examined in this study afforded 1-allyl-3-methylindoline in significantly higher ee than previously observed for the cyclization of 1 in the presence of the benchmark ligand (-)-sparteine, several ligands, structurally unrelated to sparteine and available in either enantiomeric form, were found to match the utility of (-)-sparteine in this chemistry.

Citations

Apr 28, 2011·Acta Crystallographica. Section E, Structure Reports Online·Adailton J BortoluzziAntonio C Joussef
Feb 19, 2013·Journal of the American Chemical Society·Timothy S De VriesDavid B Collum
Mar 19, 2013·Beilstein Journal of Organic Chemistry·Asier Gómez-SanjuanEsther Lete
Nov 12, 2015·Journal of the American Chemical Society·Kyoung Joo Jin, David B Collum
Apr 11, 2017·The Journal of Organic Chemistry·Hélène GuyonAnne-Sophie Castanet
Mar 21, 2007·Chemistry : a European Journal·Roberto SanzJosé Barluenga
Aug 30, 2008·Chemical Communications : Chem Comm·Anne-Marie L Hogan, Donal F O'Shea
Apr 2, 2019·Chemical & Pharmaceutical Bulletin·Hideyuki ShinoharaShinichi Miyairi
Jan 21, 2021·The Journal of Organic Chemistry·Ryan A Woltornist, David B Collum
Mar 4, 2008·The Journal of Organic Chemistry·Anne-Marie L Hogan, Donal F O'Shea
Dec 18, 2007·Chemical Reviews·Jean-Claude Kizirian
Oct 13, 2010·Journal of the American Chemical Society·Giorgio CarboneGöran Hilmersson
Jun 30, 2011·Chemical Reviews·Oleksandr O GrygorenkoIgor V Komarov
Apr 4, 2013·The Journal of Organic Chemistry·Manas K Ghorai, Y Nanaji

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