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Catalytic Enantioselective Conjugate Addition of Stereodefined Di‐ and Trisubstituted Alkenylaluminum Compounds to Acyclic Enones
Author(s) -
McGrath Kevin P.,
Hubbell Aran K.,
Zhou Yuebiao,
Santos Damián Padín,
Torker Sebastian,
Romiti Filippo,
Hoveyda Amir H.
Publication year - 2020
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.201901435
Subject(s) - chemistry , enantioselective synthesis , conjugate , moiety , catalysis , carbene , yield (engineering) , combinatorial chemistry , stereochemistry , copper , organic chemistry , mathematical analysis , materials science , mathematics , metallurgy
Catalytic enantioselective conjugate addition (ECA) reactions with readily accessible and stereochemically defined E ‐, Z ‐, di‐ and trisubstituted alkenyl aluminum compounds are disclosed. Transformations are promoted by various NHC‐copper catalysts (NHC=N‐heterocyclic carbene), which are derived from enantiomerically pure sulfonate imidazolinium salts. The desired products were obtained in up to 89% yield and >99:1 e.r.; the alkenyl moiety was transferred with complete retention of its stereochemical identity in all instances. The scope and limitations of the approach, key mechanistic attributes, and representative functionalization are presented as well.