Hydrolytic kinetic resolution of terminal mono- and bis-epoxides in the synthesis of insect pheromones: routes to (−)-( R )- and (+)-( S )-10-methyldodecyl acetate, (−)-( R )-10-methyl-2-tridecanone, (−)-( R )-( Z )-undec-6-en-2-ol (Nostrenol), (−)-(1 R ,7 R )-1,7-dimethylnonyl propanoate, (−)-(6 R ,12 R )-6,12-dimethylpentadecan-2-one, (−)-(2 S ,11 S )-2,11-diacetoxytridecane and (+)-(2 S ,12 S )-2,12-diacetoxytridecane

Metathesis-Mediated Synthesis of (R)-10-Methyl-2-tridecanone, the Southern Corn Rootworm Pheromone

“…3) A number of syntheses of (R)-1 have been reported [4][5][6][7][8] since then, including our own. 5) Chen and co-workers published in 2009 an asymmetric synthesis of (R)-1 employing a stoichiometric amount of a chiral auxiliary.…”

“…It was then diluted with an ice-dil. (R)-6-Methyl-1-nonene (7). A solution of the Grignard reagent (2.8 eq.)…”

Highly enantioselective resolution of terminal epoxides with cross-linked polymeric salen–Co(III) complexes

“…(entries 1-8) When the reaction was performed at lower temperature, a little longer time was needed and the enantioselectivities were the same (entries 9-12). Most of the crosslinked polymer catalysts showed better activities than those of the oligomeric one (tri/ di=0/100), which means the crosslinker we employed have some positive effects on the cooperation between metal centers (entries 1, 13, 17) The complete crosslinked polymeric catalyst showed slightly lower activities and enantioselectivities in the HKR of three substrates (entries 8,12,16,20) we think that the poor solubility and some unknown reactive centers of the crosslinked polymeric catalyst ought to be responsible for this result. Using the recollected catalysts for another reaction has not been successful even with the Scheme 1.…”

“…The mechanism of the reaction has proven to involve cooperative bimetallic catalysis. [3][4][5][6][7][8][9] Many groups have devoted their efforts to developing heterogeneous analogs of the typical salen-Co(III) catalyst including organic or inorganic supported catalysts, 10-12 dimeric catalysts, 13 dendrimeric catalysts, 14 oligomeric catalysts, 15,16 FBS (Fluorous Biphase Systems) 17 and ionic liquid 18 for both academic and practical reasons. Among those reports mentioned above, Jacobsen's oligomeric catalysts (Fig.…”

Highly Enantioselective Resolution of Terminal Epoxides with Cross‐Linked Polymeric Salen—Co(III) Complexes.

“…The mechanism of the reaction has proven to involve cooperative bimetallic catalysis. [3][4][5][6][7][8][9] Many groups have devoted their efforts to developing heterogeneous analogs of the typical salen-Co(III) catalyst including organic or inorganic supported catalysts, [10][11][12] (Fig. 2) exhibits exciting results, in which both the linkage length between metal centers and the counterions were carefully tuned to achieve an activity 100 times higher than that of the typical salenCo(III) complex (Fig.…”