Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers

Journal of the American Chemical Society
Lihua YuanBing Gong

Abstract

Highly efficient, one-step macrocyclizations leading to the formation of macrocyclic hexa(aramides) in high yields (69-82%) are described. The one-step macrocyclizations were facilitated by the preorganization or folding of the backbones of uncyclized precursors in the course of macrocyclization. The preorganization of backbones was achieved by the presence of localized three-centered hydrogen bonds that were adopted in the design of a class of closely related, backbone-rigidified foldamers. The macrocyclization involved reactions between diacid chloride 1 and diamine 2. The crude reaction mixtures and products were conveniently examined by mass spectrometric method (MALDI-TOF). Compared to most traditional one-step macrocyclizations that usually require high dilution conditions and often lead to very low overall yields of the desired products, cyclic hexamers 3 were obtained as the overwhelmingly major product under a variety of reaction conditions, suggesting the generality of this approach.

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Citations

Aug 9, 2012·Chemical Reviews·Dan-Wei ZhangZhan-Ting Li
Jul 26, 2005·Chemical Communications : Chem Comm·Lan HeBing Gong
Sep 22, 2005·Chemical Communications : Chem Comm·Adam R SanfordBing Gong
Nov 25, 2005·Chemical Communications : Chem Comm·Liyan XingLouis A Cuccia
May 31, 2007·Chemical Communications : Chem Comm·Fred CampbellAndrew J Wilson
Feb 24, 2010·Chemical Communications : Chem Comm·Xin Zhao, Zhan-Ting Li
Feb 8, 2011·Chemical Communications : Chem Comm·Bo QinHuaqiang Zeng
Oct 22, 2011·Chemical Communications : Chem Comm·Zhiyun DuHuaqiang Zeng
Jan 19, 2012·Chemical Communications : Chem Comm·Xiangxiang WuBing Gong
Jul 15, 2011·Acta Crystallographica. Section E, Structure Reports Online·Peishen LiWen Feng
Feb 16, 2016·Journal of the American Chemical Society·Xiaoxi WeiBing Gong
May 10, 2017·Organic & Biomolecular Chemistry·Harekrushna BeheraNandita Madhavan
Jan 1, 2015·Chemical Science·Mark A KlineBing Gong
Oct 26, 2016·Organic & Biomolecular Chemistry·Vicky Ziman ZengTianhu Li
Sep 27, 2006·Angewandte Chemie·Carmen RotgerAntoni Costa
Apr 19, 2007·Chemistry, an Asian Journal·Zhan-Ting LiHui-Ping Yi
Mar 27, 2009·Angewandte Chemie·Joseph S FergusonBing Gong
Aug 27, 2009·Organic & Biomolecular Chemistry·Kazuhiro YamatoBing Gong
Sep 12, 2009·Chemistry : a European Journal·James J MousseauLouis A Cuccia
Aug 14, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Yibing WangChen Wang
Aug 27, 2013·Chemical Communications : Chem Comm·Yibao LiQingdao Zeng
Jan 3, 2014·Chemistry : a European Journal·Chun-Fang WuZhan-Ting Li
Oct 30, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Dan-Wei ZhangZhan-Ting Li
Jan 16, 2013·Chemical Communications : Chem Comm·Haoliang FuHuaqiang Zeng

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