High diastereoselection in the aldol reaction of the bistrimethylsilyl enol ether of methyl acetoacetate with 2-benzyloxyhexanal: synthesis of (–)-pestalotin
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 693-700
- https://doi.org/10.1039/p19920000693
Abstract
Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride. The stereocontrolled synthesis of (–)-pestalotin 7 has been achieved.Keywords
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