3,3-Diethoxypropyl-lithium: a masked lithium propanal homoenolate in organic synthesis
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3113-3117
- https://doi.org/10.1039/p19880003113
Abstract
3,3-Diethoxypropyl-lithium is prepared by lithiation of the corresponding chlorinated precursor with lithium naphthalenide at –78 °C; the reaction of this masked propanal homoenolate with different electrophilic reagents [H2O, D2O, (PhCH2)2S2, PrCHO, BuiCHO, PhCHO, n-C7H15CHO, PhCHCHCHO, [[graphic omitted]O, [[graphic omitted]O, PhCOMe, PhCHNPh, PhCONEt2, PhCN, c-C6H4CN, 4-MeC6H4CN] leads to the corresponding mono- and bi-functionalized compounds. In the case of the reaction with aldehydes or ketones the prepared crude products are oxidized with m-chloroperbenzoic acid, yielding directly the γ-substituted butyrolactones.Keywords
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