Asymmetric Organocatalytic Synthesis of trans-3,4-Disubstituted Isochromanones via an Intramolecular Aldol Reaction

作者：Fronert Jeanne; Bisschops Tom; Cassens Sasse Elisa; Atodiresei Iuliana; Enders Dieter^*

来源：Synthesis, 2013, 45(12): 1708-1712.

DOI：10.1055/s-0033-1338742

• organocatalysis
• aldol reaction
• asymmetric synthesis
• dihydroisocoumarin
• enamine activation

The diastereo- and enantioselective synthesis of 3-acetyl-4-hydroxyisochroman-1-ones via an intramolecular trans-selective aldol reaction employing proline-type organocatalysts is described. Good yields (64-88%) and high stereoselectivities (87 to >95% de, 84-99% ee) are obtained, thus potentially enabling, for example, a new direct entry to carbazolelactone alkaloid natural products.

• 出版日期2013-6