A series of highly functionalized carbocycles was efficiently prepared via the selective cyclisation of unsaturated acetals and ketals in the presence of only 1 mol% of Bi(iii) or Fe(iii) triflates as the catalysts at room temperature, with yields ranging from 60 to 90%.
A new, convergent synthesis of (±)‐methyl jasmonate is presented. The strategy is based on a C4+C6 synthon approach. The C4 fragment N,4,4‐trimethoxy‐N‐methyl‐butanamide (5) was prepared in 4 steps starting from chloroacetyl chloride via the previously unreported N,4,4‐trimethoxy‐N‐methylbut‐2‐enamide (4). The coupling of 5 with the C6 synthon, cis‐3‐hexenyl magnesium chloride (6), provided easy access to (Z)‐4‐oxodec‐7‐enal (8). The latter was converted to the key intermediate (Z)‐2‐(pent‐2‐en‐1‐yl)cyclopent‐2‐en‐1‐one (9) from which (±)‐methyl jasmonate can be obtained in high yield using well‐established procedures.
A series of novel‐substituted cyclohexane derivatives has been prepared and their olfactory evaluation is presented. The different structures are derived from the cyclization of an unsaturated ketal under catalytic conditions. Its further functionalization allowed for the preparation of a series of 22 new compounds. Most of the new cyclic compounds present fruity and/or woody notes.
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