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Synlett 2001; 2001(8): 1293-1295
DOI: 10.1055/s-2001-16058
DOI: 10.1055/s-2001-16058
letter
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Enantioselective Synthesis of Cyclohexenylalkenes by Asymmetric Deprotonation of 4-tert-Butylcyclohexanone Followed by O-Nonaflation and Heck Couplings
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2001 (online)
![](https://www.thieme-connect.de/media/synlett/200108/lookinside/thumbnails/10.1055-s-2001-16058-1.jpg)
Formation of (S)-4-tert-butylcyclohex-1-enyl nonaflate 4 by reaction with nonafluorobutanesulfonyl fluoride was found to be highly enantioselective both from (S)-4-tert-butyl-1-(trimethyl-siloxy)cyclohexene 3 and from the corresponding lithium enolate 2. The latter was generated by kinetic deprotonation of 4-tert-butylcyclohexanone 1 with lithium (R,R′)-bis(1-phenylethyl)amide as enantiopure base. A number of functionalized 2-(4-tert-butylcyclohex-1-enyl)alkenes 6 were prepared with roughly 90% enantiomeric excess from trimethylsilyl enol ether 3 using a one-pot nonaflation/Heck reaction sequence.
enantioselective deprotonation - silyl enol ethers - alkenyl nonaflates - Heck reaction - 1,3-dienes