Diexo-3-aminonorbornane-2-carboxylic acid as highly applicable chiral source for the enantioselective synthesis of heterocycles

作者：Fulop Ferenc^*; Miklos Ferenc; Forro Eniko

来源：Synlett, 2008, (11): 1687-1689.

DOI：10.1055/s-2008-1077793

• asymmetric synthesis
• beta-amino acids
• retro reactions
• ring closure
• chiral source
• chirality transfer
• domino reactions

Diastereomers of tetracyclic pyrrolopyrimidine derivatives 2 and 3 were prepared in a three-step dornino reaction from diexo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide with levulinic acid or p-toluoylpropionic acid. When subjected to a microwave-mediated retro-Diels-Aider reaction, these tetracycles furnished bicyclic pyrrolo[1,2-a]pyrimidines through the loss of cyclopentadiene. When enantiomeric diexo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide was used, the products were enantiomeric heterocycles with ee > 99%, demonstrating that the title compound is an excellent chiral Source.

• 出版日期2008-7-1