Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.
A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range of alkenes, and the reaction was performed at room temperature. 1-Nitrocyclopropyl esters are versatile building blocks to access the corresponding cyclopropane amino esters and aminocyclopropanes in two and three steps, respectively, from commercially available products.
Moreau
Benoît
B
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Charette
André B
AB
D000085:Acetates / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D000475:Alkenes; D000596:Amino Acids; D003521:Cyclopropanes; C025733:nitroacetic acid methyl ester; D007455:Iodine