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Organocatalytic Asymmetric Synthesis of an Advanced Intermediate of (+)‐Sarain A
Author(s) -
Hu XiuNing,
Wu DongPing,
Xu YePeng,
Huang PeiQiang
Publication year - 2021
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.202004261
Subject(s) - enantioselective synthesis , hydrosilylation , chirality (physics) , catalysis , chemistry , organocatalysis , transfer hydrogenation , combinatorial chemistry , michael reaction , stereochemistry , organic chemistry , physics , chiral symmetry , quark , quantum mechanics , ruthenium , nambu–jona lasinio model
The first organocatalytic asymmetric synthesis of an advanced intermediate of (+)‐sarain A was achieved. This approach featured the employment of an organocatalytic asymmetric Michael addition reaction and a nitrogen‐to‐carbon chirality transfer to forge three chiral centers, as well as a catalytic hydrosilylation for the chemoselective reduction of a key lactam intermediate. The tricyclic intermediate contained all the required functionalities for elaborating into (+)‐sarain A.
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