Ligand (biochemistry)

Receptor

Organic chemistry

Combinatorial chemistry

Stereochemistry

Enantioselective synthesis

Catalysis

Chemistry

Chiral ligand

Enantiomer

Biochemistry

Organic Letters

[reaction: see text]. Hydroxymethylallenes are efficiently converted to the corresponding spiropentanes in high yields and enantiomeric ratios upon treatment with Zn(CH2I)2 and dioxaborolane ligand 1. The reaction also proceeds with complete diastereocontrol. The application of this methodology to the synthesis of spiropentaneacetic acid is also presented.

Enantioselective Synthesis of Spiropentanes from Hydroxymethylallenes