99% chirally selective synthesis via pinanediol boronic esters: insect pheromones, diols, and an amino alcohol

DS Matteson, KM Sadhu…

文献索引：Matteson,D.S.; Sadhu,K.M.; Peterson,M.L. Journal of the American Chemical Society, 1986 , vol. 108, p. 810

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被引用次数: 155

摘要

Abstract: Chiral selectivities generally exceed 99% in the homologation of (+)-pinanediol alkylboronates (1) to (lS)-(1-chloroalky1) boronates (3) by reaction of 1 with (dichloromethy1) lithium at-100 OC followed by zinc chloride catalyzed rearrangement of the resulting borate complexes (2) at 0-25 OC. Diastereoselectivity falls to 95.7% with the methylboronate.(-)-Pinanediol leads to the 1R isomers. Nucleophilic displacements on (I- ...