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The addition of the prenyl cation to prenyl thiol acetate
β Scribed by Kunihiko Takabe; Takao Katagiri; Juntaro Tanaka
- Publisher
- Elsevier Science
- Year
- 1971
- Tongue
- French
- Weight
- 188 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
It haa been Imown that prenyl halides (3-methyl-2-butenyl halide81 ') and prenyl acetate 2) were dimeriaed to the lavandulyl compounde, the 4,3-coupling monoterpenee, eeleotively by the a&ion of the acid& In the oaae of prenyl thiol aoetate (I), S-lavandulyl compound6 could be obtained hardly and the sulfide thiol acetate (II) was a main product (cf. Table
2) (Beaction A).
The reaction of prenyl aoetate with (I) by aluminium chlo-5o"c),
π SIMILAR VOLUMES
At elevated temperature (refluxing THF) prenyl anion adds regio- and enantioselectively to aldehyde 1 when a chiral, borneol-derived ligand is present. This reaction is the key stepin the first total synthesis of the monoterpene (-)-rosiridol (retrosynthesis is shown on the right). In addition, the
Unsymmetrically substituted fumaric esters underwent highly regioselective conjugate addition of thiols in the presence of a lithium cation in non-coordinative media.