Journal of Organic Chemistry p. 14723 - 14732 (2018)
Update date:2022-08-29
Topics:
Fulton, Tyler J.
Alley, Phebe L.
Rensch, Heather R.
Ackerman, Adriana M.
Berlin, Cameron B.
Krout, Michael R.
Monoorganozinc reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38-99% yields and 9:1-20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol that harnesses in situ generated monoorganozinc reagents delivers comparable product yields.
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