Asymmetric 1,4-additions to γ-menthyloxybutenolides. Enantiospecific synthesis of chiral 1,4-butanediols

✍ Scribed by Johan F.G.A. Jansen; Ben L. Feringa

• Book ID: 104233042
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 182 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80599-2

✦ Synopsis

Optically active methyl-substituted butanediols and d/-lactones were prepared from [-menthyloxy-2[5HJ-furanone. Chiral [-menthyloxybutenolides (1) have served as the basis for our novel asymmetric synthesis strategies= due to the excellent stereocontrol by the J-menthyloxy substituent, the easy way of preparation of these synthons in enantiomerically pure form and the use of cheap d-or l-menthol as chiral auxiliary. Optically active f-lactones 2 can be particularly advantageous in the formation of acyclic chiral building blocks with arrays of methyl-and hydroxy-substituents at vicinal or remote chiral centers. For instance

Hanessian and co-workers3 reported the use of (S)-4-hydroxymethyl-