DTBB-catalysed lithiation of 4-functionalised 1-chloro-2-butenes
✍ Scribed by Fernando F Huerta; Cecilia Gómez; Miguel Yus
- Book ID
- 107857968
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 704 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0040-4020
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📜 SIMILAR VOLUMES
The reaction of 6-chloro-1-hexene 1 with lithium powder and a catalytic amount of 4,4%-di-tert-butylbiphenyl (DTBB, 5% molar) in THF at -78°C gives the corresponding organolithium intermediate 2, which by reaction with different electrophiles [Bu t CHO, PhCHO, Et 2 CO, (CH 2 ) 5 CO, PhCOMe] affords,
Vinylic lithium reagents 1 and 2 could be obtained by the title procedure from their chloro precursors 5 and 6 instead of the less stable corresponding bromo derivatives 3 and 4. Condensation with carbonyl compounds leads to interesting synthetic applications such as a two steps synthesis of retinal
a synthetic method for the preparation of the acetate of (Z)-4-chloro-2-methyl-2-butenl-01, a precursor of the (Z)-hydroxy prenyl synthon 1s described The use of such synthon In the preparation of a metabollte of a prenyl-contalnlng substance 1s also Illustrated The hemlterpenold group (lsopenteny