80325-80-0

Upstream product

• 42558-54-3 Methyl 4-methyl-3-oxopentanoate 
• 54876-99-2 4-methylpentane-1,3-diol 
• 100-39-0 benzyl bromide 
• 75-24-1 trimethylaluminum 
• 80325-78-6 (2S,3S)-2-(2-Benzyloxy-ethyl)-3-methyl-oxirane 
• 80325-78-6 (3RS,4SR)-1-(benzyloxy)-3,4-epoxypentane 

Downstream Products

• 128886-25-9 t-Butyl (4-methyl-1-tosyloxypentane-3-yloxy)acetate 

Relevant academic research and scientific papers

Hemilabile Benzyl Ether Enables Γ-C(sp3)-H Carbonylation and Olefination of Alcohols

Pd-catalyzed C(sp3)-H activation of alcohol typically shows β-selectivity due to the required distance between the chelating atom in the attached directing group and the targeted C-H bonds. Herein we report the design of a hemilabile directing group which exploits the chelation of a readily removable benzyl ether moiety to direct Γ- or δ-C-H carbonylation and olefination of alcohols. The utility of this approach is also demonstrated in the late-stage C-H functionalization of β-estradiol to rapidly prepare desired analogues that required multi-step syntheses with classical methods.

Hemilabile Benzyl Ether Enables γ-C(sp3)-H Carbonylation and Olefination of Alcohols

Pd-catalyzed C(sp3)-H activation of alcohol typically shows β-selectivity due to the required distance between the chelating atom in the attached directing group and the targeted C-H bonds. Herein we report the design of a hemilabile directing group which exploits the chelation of a readily removable benzyl ether moiety to direct γ- or δ-C-H carbonylation and olefination of alcohols. The utility of this approach is also demonstrated in the late-stage C-H functionalization of β-estradiol to rapidly prepare desired analogues that required multi-step syntheses with classical methods.