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Catalytic Generation of C1 Ammonium Enolates from Halides and CO for Asymmetric Cascade Reactions
Author(s) -
Li LuLu,
Ding Du,
Song Jin,
Han ZhiYong,
Gong LiuZhu
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901501
Subject(s) - carbonylation , catalysis , chemistry , halide , cascade , enantioselective synthesis , cascade reaction , carbon monoxide , combinatorial chemistry , palladium , organic chemistry , chromatography
A general strategy for the design of asymmetric cascade reactions using readily available halides and carbon monoxide (CO) as substrates is developed. The key is the catalytic generation of C1‐ammonium enolates for the subsequent asymmetric cascade reactions through the combination of palladium‐catalyzed carbonylation and chiral Lewis base catalysis. Utilizing this strategy, we have established asymmetric formal [1+1+4] and [1+1+2] reactions to afford chiral dihydropyridones and β‐lactams with high yields and high enantio‐ and diastereoselectivities.