104897-87-2Relevant academic research and scientific papers
Camphorsulfonamide-Shielded, Asymmetric 1,4-Additions and Enolate Alkylations; Synthesis of a Southern Corn Rootworm Pheromone
Oppolzer, Wolfgang,Dudfield, Philip,Stevenson, Thomas,Godel, Thierry
, p. 212 - 215 (2007/10/02)
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 percent e.e.Similarly, propionates 12 yielded after deprotonation, enolate alkylation, and reductive ester cleveage the (R)-alcohols 15 in 78-98 percent e.e.The acid (+)-3e was converted to the pheromone (-)-11.
