Pyrrole derivativesR 0120 DOI: 10.1002/chin.201214107

Unusual Ester-Directed Regiochemical Control in endo-Selective Asymmetric 1,3-Dipolar Cycloadditions of Azomethine Ylides with β-Sulfonyl Acrylates. — One of the key features of this ester-controlled endo-selective 1,3-dipolar cycloaddition is that high yields and excellent selectivities are observed for a range of imino esters, especially imino esters derived from α-substituted amino acids. In the latter case, the cycloaddition affords highly substituted pyrrolidines bearing a unique nitrogen-substi-tuted quaternary stereogenic center. Subsequent transformation of the cycloadducts leads to useful cyclic imine and dihydropyrrole derivatives without loss of enantiomer-ic excess. — (TONG, M.-C.; LI, J.; TAO, H.-Y.; LI, Y.-X.; WANG*, C.-J.; Chem. Eur. J. 17 (2011) 46, 12922-12927, http://dx.doi.org/10.1002/chem.201102430 ; Coll. Chem. Mol. Sci., Wuhan Univ., Wuhan, Hubei 430072, Peop. Rep. China; Eng.) — Bartels

14- 107

ChemInform 2012, 43, issue 14 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim