Diastereoselective trimolecular condensation between indole, Meldrum's acid and chiral sugar-derived aldehydes

作者:Dardennes Emmanuel; Gerard Stephane; Petermann Christian; Sapi Janos*
来源:Tetrahedron: Asymmetry , 2010, 21(2): 208-215.
DOI:10.1016/j.tetasy.2009.12.017

摘要

The trimolecular condensation of indole, Meldrum's acid and chiral, sugar-derived aldehydes took place in good yield and high diastereoselectivity. The absolute configuration of the alpha-carbon of the chiral aldehydes ensured a predictable diastereocontrol of the newly created stereogenic centre except for (3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde 3i. In this case, the opposite stereochemistry may be explained by a less congested conformer of the Knoevenagel-adduct intermediate.

  • 出版日期2010-2-22