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Rhodium‐Catalyzed Asymmetric N−H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (−)‐Chaetominine
Author(s) -
Zhou Yirong,
Breit Bernhard
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705059
Subject(s) - enantioselective synthesis , rhodium , allylic rearrangement , catalysis , surface modification , chemistry , denticity , combinatorial chemistry , total synthesis , formal synthesis , organic chemistry , metal
An unprecedented asymmetric N−H functionalization of quinazolinones with allenes and allylic carbonates was successfully achieved by rhodium catalysis with the assistance of chiral bidentate diphosphine ligands. The high efficiency and practicality of this method was demonstrated by a low catalyst loading of 1 mol % as well as excellent chemo‐, regio‐, and enantioselectivities with broad functional group compatibility. Furthermore, this newly developed strategy was applied as key step in the first enantioselective formal total synthesis of (−)‐chaetominine.