Tandem homologation-acylation chemistry: Single and double homologation

TETRAHEDRON

卷:91

Article

Henderson, Carley S.¹  Mazzone, Jennifer R.¹  Moore, Amanda M.¹  Zercher, Charles K.¹ 

[1] Univ New Hampshire, Dept Chem, Durham, NH 03824 USA

关键词: Zinc carbenoid;    Homologation;    Acylation;   

DOI  :  10.1016/j.tet.2021.132223

来源: Elsevier

【 摘 要 】

Treatment of beta-dicarbonyls with the Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both gamma-dicarbonyl functionality and beta-dicarbonyl functionality. In situ exposure of the acylated product to additional zinc carbenoid effects a second regiospecific homologation reaction. (C) 2021 Elsevier Ltd. All rights reserved.

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