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  • Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.

Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.

Journal of the American Chemical Society (2005-12-22)
Benoît Moreau, André B Charette
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline], 97%
Sigma-Aldrich
Methyl nitroacetate, 98%