The Reaction of α,β-Acetylenic Ketones with Dicyclohexylborane: Stereoselective Synthesis of Functionalized Trisubstituted Olefins. -α,β-Acetylenic ketones (I) (6 compounds) undergo 1,4-addition of dicyclohexylborane to give allenoxyborinate intermediates which react with excess starting ketone to
The reaction of α,β-acetylenic ketones with dicyclohexylborane: Stereoselective synthesis of functionalized trisubstituted olefins
✍ Scribed by George W. Kabalka; Su Yu; Nan-Sheng Li; Ute Lipprandt
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 187 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Allenoxyborinates, easily generated via the 1,4-addition of dicyclohexylborane to a,~acetylenic ketones, react in situ with excess starting ketone to afford stereodefined, functionalized trisubstituted olefins in high yields.
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We wish to report that p-toluenesulfonylhydrazones of certain o,g%poxyketones undergo a novel fragmentation reaction to yield an acetylene and a ketone as shown in Scheme 1.
## Abstract Stereoselective construction of trisubstituted alkenes has wide applicability to the synthesis of many natural products Specifically, β‐disubstituted enones are important functionalized trisubstituted alkene targets. The reaction of organocerium reagents with secondary β‐enamino ketones