18432-37-6Relevant articles and documents
Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent suzuki cross-couplings
Zultanski, Susan L.,Fu, Gregory C.
supporting information; experimental part, p. 15362 - 15364 (2011/11/11)
With the aid of a chiral nickel catalyst, enantioselective γ- (and I-) alkylations of carbonyl compounds can be achieved through the coupling of γ-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.
A mild biosynthesis of lactones via enantioselective hydrolysis of hydroxynitriles
Pollock, Julie A.,Clark, Karen M.,Martynowicz, Bethany J.,Pridgeon, Matthew G.,Rycenga, Matthew J.,Stolle, Kristen E.,Taylor, Stephen K.
, p. 1888 - 1892 (2008/02/12)
We have developed a biocatalytic method to produce lactones and related compounds via the enzymatic hydrolysis of γ- and β-hydroxynitriles. The synthesis is a mild, general, and environmentally friendly way to enantioselectively hydrolyze nitriles with commercially available nitrilase enzymes. The synthesis of four pheromones is demonstrated via a one-step method.
Synthesis of natural (-)-hamigeran B
Clive, Derrick L.J.,Wang, Jian
, p. 7731 - 7733 (2007/10/03)
Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (-)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe 2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic C-O bond from hydrogenolysis.
