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Synlett 2001; 2001(8): 1293-1295
DOI: 10.1055/s-2001-16058
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Enantioselective Synthesis of Cyclohexenylalkenes by Asymmetric Deprotonation of 4-tert-Butylcyclohexanone Followed by O-Nonaflation and Heck Couplings

Ilya M. Lyapkalo* , Matthias Webel, Hans-Ulrich Reissig
  • *Freie Universität Berlin, Institut für Chemie - Organische Chemie, Takustr. 3, 14195 Berlin, Germany; Fax + 49-(0)30/83 85-53 67; E-mail: hans.reissig@chemie.fu-berlin.de
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Publication Date:
31 December 2001 (online)

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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

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