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

W Oppolzer, P Dudfield, T Stevenson…

文献索引：Oppolzer, Wolfgang; Dudfield, Philip; Stevenson, Thomas; Godel, Thierry Helvetica Chimica Acta, 1985 , vol. 68, p. 212 - 215

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被引用次数: 116

摘要

Abstract Using readily accessible 10-sulfonamido-isoborneols as regenerable, chiral auxiliaries, highly face-selective C–C-bond formations at C α and C β of carboxylates could be conveniently achieved. Thus, conjugated additions of RCu to enoates (1 [RIGHTWARDS ARROW] 2) furnished, after saponification, β-substituted carboxylic acids 3 in 94–98% ee Similarly, propionates 12 yielded after deprotonation, enolate alkylation, and reductive ...