Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group

Angewandte Chemie
Jignesh J PatelVictor Snieckus

Abstract

A general synthesis of highly substituted 2-naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z-cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation for ring closure to give the aryl 2-naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one-pot process. Mechanistic insight into the remote lateral metalation step, demonstrating the requirement of Z-cinnamamide, is described. Application of this methodology to the synthesis of highly substituted 3,3'-diaryl BINOL ligands is also reported.

References

Aug 3, 2002·Organic Letters·Anucha Namsa-aid, Somsak Ruchirawat
Mar 13, 2003·Chemical Reviews·Deevi BasavaiahTummanapalli Satyanarayana
Aug 14, 2003·Chemical Reviews·Yu ChenAndrei K Yudin
Sep 27, 2003·The Journal of Organic Chemistry·Quan-Zhong LiuYao-Zhong Jiang
Mar 10, 2005·Chemical Reviews·Jean Michel Brunel
Jan 26, 2007·Organic Letters·Evan S DivirgilioMarisa C Kozlowski
Dec 5, 2008·Journal of the American Chemical Society·Cuixiang SunAndrew G Myers
Apr 14, 2009·Journal of the American Chemical Society·Hiromichi Egami, Tsutomu Katsuki
Oct 23, 2009·Chemical Society Reviews·Marisa C KozlowskiElizabeth C Linton
Jul 16, 2010·Bioorganic & Medicinal Chemistry Letters·Marina RoussakiAnastasia Detsi
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
May 11, 2012·Angewandte Chemie·Carin C C Johansson SeechurnVictor Snieckus
Dec 14, 2016·Journal of the American Chemical Society·Sachin NaruteDoron Pappo

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