Zinc-mediated highly α-regioselective prenylation of imines with prenyl bromide.

Zinc-mediated highly α-regioselective prenylation of imines with prenyl bromide.

Organic letters (2012-01-24)

Li-Ming Zhao, Shu-Qing Zhang, Hai-Shan Jin, Li-Jing Wan, Fei Dou

ABSTRACT

A highly α-regioselective prenylation of imines has been successfully developed. The efficiency of this approach is confirmed by a wide range of imines including N- and C-aryl aldimines, N-alkyl aldimines, C-alkyl aldimines, and N- and C-aryl ketimines. The approach uses prenyl bromide as the prenyl source and inexpensive and convenient zinc as the mediator as well as environmentally benign 1,3-dimethyl-2-imidazolidinone (DMI) as the solvent.

MATERIALS

Product Number

Brand

Product Description

193453

Sigma-Aldrich

1,3-Dimethyl-2-imidazolidinone, reagent grade

40727

Sigma-Aldrich

1,3-Dimethyl-2-imidazolidinone, ≥99.0% (GC)

40725

Sigma-Aldrich

1,3-Dimethyl-2-imidazolidinone, absolute, over molecular sieve (H₂O ≤0.04%), ≥99.5% (GC)