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Synthesis 2001; 2001(3): 0483-0486
DOI: 10.1055/s-2001-11445
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A Multigram, Catalytic and Enantioselective Synthesis of Optically Active 4-Methyl-2-cyclohexen-1-one: a Useful Chiral Building Block

Fabio Bertozzi* , Paolo Crotti, Ben L. Feringa, Franco Macchia, Mauro Pineschi
  • *Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy; Fax + 39 05 04 33 21; E-mail: pineschi@farm.unipi.it
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Publication Date:
31 December 2001 (online)

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The first catalytic asymmetric synthesis of both (R)-(+)- and (S)-(-)-4-methyl-2-cyclohexen-1-one and a new and improved synthesis of both enantiomers of (1S,4S)-(-) and (1R,4R)-(+)-4-methyl-2-cyclohexen-1-ol was developed on a multigram scale. The key step of this approach is the asymmetric catalyzed addition of Me2Zn (SN2′-pathway) to racemic 1,3-cyclohexadiene monoepoxide. This step has been optimized as for as enantio- and regioselectivities, and work-up procedures. The striking ligand accelerated catalysis exhibited by the chiral copper complex of the 2,2′-binaphthyl-based phosphoramidite, herein reported, permitted a very low catalyst loading (0.6 mol%).

enantiomer resolution - scale-up - catalysis - organozinc reagent - copper