On the lithium dimethylcuprate induced conversion of propargylic esters into allenes using a steroidal C/D fragment derived from vitamin D3 as a stereochemical probe.
✍ Scribed by Alberto Haces; Eugéne M.G.A. van Kruchten; William H. Okamura
- Book ID
- 104220936
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 257 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
summaq: The reactions of (CH3)2CuLl with various C-8 epuneric propargyllc esters derived from Grundmann's ketone, a C/D steroad fragment orlglnating from vltanun D3, lead to the corresponctrng allenes, the stereochermstry of which ln&cate a preferred ant1 1,3-substltutlon.
A very recent communication on the revlslon of literature data by Vermeerl prompts us to disclose our results In this field. There exists some confusion as to whether the organocopper promoted conversion of propargyllc esters into the corresponding allenlc compounds proceeds either by a -or an antz attack of the copper reagent2 (Scheme 1). Until recently, the