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Enantioselective Conjugate Additions of “Difficult” Ketones to Nitrodienynes and Tandem Annulations
Author(s) -
Liu Teng,
Zhou Mingxin,
Yuan Tengrui,
Fu Binbin,
Wang Xinran,
Peng Fangzhi,
Shao Zhihui
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600849
Subject(s) - enantioselective synthesis , chemistry , conjugate , tandem , catalysis , amine gas treating , combinatorial chemistry , acetone , organic chemistry , mathematical analysis , materials science , mathematics , composite material
The first enantioselective conjugate additions of problematic aromatic ketones and acetone to nitrodienynes have been achieved by employing a chiral multifunctional primary amine catalyst recently developed by us. The reactions took place in a 1,4‐manner. Furthermore, by utilizing the resulting chiral functionalized 1,3‐enynes as a starting point, we have developed unprecedented p ‐toluenesulfonic acid‐catalyzed tandem annulations, which allow the efficient and selective construction of various synthetically useful cyclic 1,5‐diketones (R=Ar) and dienones (R=Me).