Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by <i>N</i>,<i>N-</i>Dimethylacetamide
作者:Tyler J. Fulton、Phebe L. Alley、Heather R. Rensch、Adriana M. Ackerman、Cameron B. Berlin、Michael R. Krout
DOI:10.1021/acs.joc.8b02201
日期:2018.12.7
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
易于从烷基溴化物中获得的单有机锌试剂,在存在铜(Ⅰ)和铜(Ⅱ)盐的情况下,与β,β-二取代的烯酮和TMScl具有优异的反应活性,可以在38-99的范围内合成各种环状官能化的β-季酮。 %的收率和9:1–20:1的非对映选择性。使用溴化单有机锌试剂可显着改善共轭物的DMA。利用原位生成的单有机锌试剂的简单一锅操作方案可提供相当的产品产量。