Regioselectivity of the reactions of trialkylaluminum reagents with 2,3-epoxyalcohols: Application to the synthesis of α-chiral aldehydes

Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product

“…O -Methylation, cleavage of the THP ether, and stereospecific reduction of the alkyne provided the allylic alcohol 252 . Sharpless asymmetric epoxidation of 252 was followed by regioselective methylation of the resultant epoxy alcohol [ 173 ] to afford the 1,2-diol 253 with the C9 stereogenic center established. Treatment of 253 with I 2 , Ph 3 P, and imidazole [ 174 ] and subsequent desilylation delivered the alcohol 254 .…”

Trimethylaluminum

“…Trimethylaluminum aldehydes by periodate oxidation [17]. Methylation of 2,3epoxy amines with Me 3 Al occurs selectively at C-2 position with retention of the configuration at C-2 to give 2-methyl-3-amino alcohols.…”

Chiral porphyrin imine manganese complex as catalyst for asymmetric epoxidation of styrene derivatives

“…1,2 Some of the synthetic utility of chiral epoxides are as follows; conversion of chiral epoxides into hydroxy compounds through ring opening reactions, 3 carbon-carbon bond formation and formylation, 4 ringopening reactions of chiral epoxides with isocyanates to yield chiral amino alcohols, 5 Payne rearrangement of converting chiral epoxy alcohols to chiral diols, 6 meso epoxide ring opening with dithiols to form chiral disulfides, 7 rearrangement of chiral epoxides, 8 utilization of terminal epoxides in the synthesis of γ-lactones, 9 in the synthesis of 2,5-disubstituted piperdine alkaloids, 10 and in the synthesis of norlignan currculigine, which is an in vivo anti-arrhythmic active compound. 1,2 Some of the synthetic utility of chiral epoxides are as follows; conversion of chiral epoxides into hydroxy compounds through ring opening reactions, 3 carbon-carbon bond formation and formylation, 4 ringopening reactions of chiral epoxides with isocyanates to yield chiral amino alcohols, 5 Payne rearrangement of converting chiral epoxy alcohols to chiral diols, 6 meso epoxide ring opening with dithiols to form chiral disulfides, 7 rearrangement of chiral epoxides, 8 utilization of terminal epoxides in the synthesis of γ-lactones, 9 in the synthesis of 2,5-disubstituted piperdine alkaloids, 10 and in the synthesis of norlignan currculigine, which is an in vivo anti-arrhythmic active compound.…”

“…The synthetic utilities of chiral epoxides are many and therefore they are in increasing demand in pharmaceutical industries particularly in the synthesis of agrochemicals, flavors, fragrances, optically active polymers, and chiral catalysts. 1,2 Some of the synthetic utility of chiral epoxides are as follows; conversion of chiral epoxides into hydroxy compounds through ring opening reactions, 3 carbon-carbon bond formation and formylation, 4 ringopening reactions of chiral epoxides with isocyanates to yield chiral amino alcohols, 5 Payne rearrangement of converting chiral epoxy alcohols to chiral diols, 6 meso epoxide ring opening with dithiols to form chiral disulfides, 7 rearrangement of chiral epoxides, 8 utilization of terminal epoxides in the synthesis of γ-lactones, 9 in the synthesis of 2,5-disubstituted piperdine alkaloids, 10 and in the synthesis of norlignan currculigine, which is an in vivo anti-arrhythmic active compound. 11 NO synthase inhibitors can be synthesized by the ring opening reaction of chiral epoxide.…”