Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy.

Angewandte Chemie
Yate ChenWangqing Kong

Abstract

An unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.

References

Jan 19, 2000·Current Medicinal Chemistry·H SugimotoY Kawakami
Oct 4, 1996·The Journal of Organic Chemistry·Ken KokuboMasakatsu Nomura
Aug 16, 2003·The Journal of Organic Chemistry·Dinesh Kumar RayabarapuChien-Hong Cheng
Jun 26, 2004·Journal of Natural Products·Tetsuro ItoDedy Darnaedi
Nov 27, 2004·Organic & Biomolecular Chemistry·A V VasilyevA P Rudenko
Apr 10, 2007·Journal of the American Chemical Society·Yasuyuki HaradaNaoto Chatani
Sep 18, 2007·Organic Letters·Hirokazu Tsukamoto, Yoshinori Kondo
Sep 25, 2007·Angewandte Chemie·Scott A SnyderYunqing Lin
Jan 16, 2009·Journal of the American Chemical Society·Scott A SnyderAlexandros L Zografos
Nov 12, 2009·Organic Letters·Jenna L Jeffrey, Richmond Sarpong
Nov 27, 2009·Chemical Reviews·Graham E Dobereiner, Robert H Crabtree
Aug 7, 2010·Science·Andrew J A Watson, Jonathan M J Williams
Mar 25, 2011·Nature Chemistry·Joseph MoranMichael J Krische
Oct 7, 2011·Chemical Society Reviews·Ramon Rios
Feb 23, 2013·Pure and Applied Chemistry. Chimie Pure Et Appliquée·Joseph Moran, Michael J Krische
Jul 24, 2014·Bioorganic & Medicinal Chemistry Letters·Yajun ZhengSuresh B Singh
Feb 4, 2016·The Journal of Organic Chemistry·Changduo PanJin-Tao Yu
May 28, 2016·Expert Opinion on Drug Discovery·Ya-Jun Zheng, Colin M Tice
Jul 7, 2016·Chemical Communications : Chem Comm·Adrien Quintard, Jean Rodriguez
Dec 10, 2016·The Journal of Organic Chemistry·Basuli Suchand, Gedu Satyanarayana
Apr 7, 2017·Beilstein Journal of Organic Chemistry·Marika TurekPiotr Bałczewski
Jan 11, 2018·Chemical Reviews·Avelino CormaMaria J Sabater
Jun 29, 2018·Chemical Society Reviews·Aishun DingRamon Rios
Sep 18, 2018·Organic & Biomolecular Chemistry·Benjamin G Reed-BerendtLouis C Morrill

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Citations

Jul 28, 2021·The Journal of Organic Chemistry·Xiangtai MengShenlin Huang
Sep 29, 2021·Chemical Communications : Chem Comm·Yuanyuan FuShenlin Huang

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