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Enantioselective Conjugate Addition of Stabilized Arylzinc Iodide to Enones: an Improved Protocol of the Hayashi Reaction
Author(s) -
Casotti Gianluca,
Rositano Vincenzo,
Iuliano Anna
Publication year - 2021
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.202001141
Subject(s) - enantioselective synthesis , chemistry , iodide , conjugate , nucleophile , reagent , aryl , electrophile , combinatorial chemistry , halogen , organic chemistry , catalysis , alkyl , mathematical analysis , mathematics
Abstract Stabilised arylzinc iodide, prepared by direct insertion of zinc into aryl iodides, were used as nucleophiles in the Hayashi Rh‐catalysed enantioselective conjugate addition to enones. The reaction conditions were optimized in the addition of phenylzinc iodide to 2‐cyclohexen‐1‐one, obtaining good yields and 99% ee of the addition product. The general applicability of the protocol was checked using different arylzinc iodides and enones. Organometallic reagents endowed with both halogen and electrophilic groups were also successfully used.