Anti-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate
Organic Letters2000Vol. 2(19), pp. 3035–3037
Citations Over TimeTop 10% of 2000 papers
Abstract
The boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2-diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers. Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.
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