Synfacts 2010(11): 1302-1302  
DOI: 10.1055/s-0030-1258784
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Unexpected δ-Substitution Products

Contributor(s): Benjamin List, Saihu Liao
Z. Qiao, Z. Shafiq, L. Liu*, Z.-B. Yu, Q.-Y. Zheng, D. Wang, Y.-J. Chen*
Beijing National Laboratory for Molecular Science, P. R. of China
Further Information

Publication History

Publication Date:
21 October 2010 (online)

Significance

The authors report a chiral primary amine 3 catalyzed reaction of cyclic Morita-­Baylis-Hillman (MBH) adducts 1 with indoles 2, in which unexpected δ-substitution products 4 were obtained in high enantioselectivities. This transformation proceeded well in the presence of 20 mol% of primary amine catalyst 3 and 40 mol% TFA as cocatalyst at room temperature, providing various δ-substitution products 4 in high yields (68-92%) and high enantiomeric purity (er up to 96.5:3.5). N-Methylindole was less reactive and enantioselective under the same reaction conditions. The reactions of cyclohexenone-derived MBH alcohols or alkyl- instead of aryl-substituted ones did not give the desired products.