Camphorsulfonamide‐Shielded, Asymmetric 1,4‐Additions and Enolate Alkylations; Synthesis of a Southern Corn Rootworm Pheromone. Preliminary Communication

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Abstract
Using readily accessible 10‐sulfonamido‐isoborneols as regenerable, chiral auxiliaries, highly face‐selective C–C‐bond formations at Cα and Cβ of carboxylates could be conveniently achieved. Thus, conjugated additions of RCu to enoates (1→2) furnished, after saponification, β‐substituted carboxylic acids 3 in 94–98% e.e. Similarly, propionates 12 yielded after deprotonation, enolate alkylation, and reductive ester cleavage the (R)‐alcohols 15 in 78–98% e.e. The acid (+)‐3e was converted to the pheromone (–)‐11.

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