ChemInform Abstract: Asymmetric Cyclopropanation of Conjugated Cyanosulfones Using a Novel Cupreine Organocatalyst: Rapid Access to δ³‐Amino Acids.

Abstract

 3 -Amino Acids. -The cyclopropanation of cyanosulfones (I) in the presence of a new cupreine catalyst (PQN) gives rise to chiral cyclopropanes (III). The magnesium-mediated desulfonylation of derivative (IIIa) is accompanied by a ring opening to afford nitrile (IV), which is converted into  3 -amino acid (VI) (yield of the reduction step is not given). The borane-mediated reduction of the nitrile group of compound (IIIa) is accompanied by cyclization to afford fused pyrrolidine (VII). -(AITKEN, L. S.; HAMMOND, L. E.; SUNDARAM, R.; SHANKLAND, K.; BROWN, G. D.; COBB*, A. J. A.; Chem. Commun. (Cambridge) 51 (2015) 70, 13558-13561, http://dx.doi.org/10.1039/C5CC05158D ; Sch. Chem., Food Pharm., Univ. Reading, Whiteknights, Reading, Berkshire RG6 6AD, UK; Eng.) -R. Staver 01-029