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Periselective and enantioselective carbonyl–ene reaction of isoprene with fluoroalkyl glyoxylate catalysed by modified binaphthol–titanium complex: asymmetric catalytic synthesis of enantiomerically pure ipsdienol

1995; Royal Society of Chemistry; Issue: 23 Linguagem: Inglês

10.1039/c39950002391

2050-5639

Masahiro Terada, Köichi Mikami,

Advanced Synthetic Organic Chemistry

The asymmetric reaction of trifluoroethyl glyoxylate 3d with isoprene 4 catalysed by the modified binaphthol–titanium complex 2b provides the ene product 5d in high periselectivity (92%) and complete enantioselectivity, which can be converted to ipsdienol 1, a component of the aggregation pheromone of the bark beetle, genus lps, in enantiomerically pure form.