Dimethyl t-butylsilyl enol ethers of cycloalkananes react with ethyl propynoore in the presence of ZrCl4 to give protected cyclobutenic hydroxy esters. Cycloproponation by cycloaddition of diazoalkanes followed by sensitized photocleavage. leads to bicycle I2.1 .O] pentan-2-ol derivatives which are
Synthesis of small rings via the protected cyanohydrin method.
โ Scribed by Gilbert Stork; Jean Claude Depezay; Jean d'Angelo
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 208 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
โฆ Synopsis
We have reported that the anion derived from the readily available protected cyanohydrins of aldehydes are generally useful as acyl carbanion equivalents and can be used in the synthesis of ketones v&, inter alia, alkylation and --Michael addition.
๐ SIMILAR VOLUMES
## SummarE Zearalenone was synthesized by a general cyclization method of orsellic acid type macrolides having ketone moiety using the intramolecular alkylation of the protected cyanohydrin. This alkylation tolerates the presence of ester group and requires short reaction time.
A facile synthesis of aryl a-keto esters is reported involving the rearrangement of aryl cyanohydrin carbonate esters induced by the a-carbanion to the nitrile group generated by LDA. However, under similar conditions, an o-benzyloxycyanohydrin carbonate ester rearranged via a domino reaction leadin