Synthesis and applications of (1R,5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol as a chiral auxiliary in Diels-Alder reactions

Article abstract of DOI:10.1016/S0957-4166(00)00242-1

A short asymmetric synthesis of (1R,5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol 7 is described along with its application as a chiral auxiliary in various Diels-Alder reactions. The enantioselectivity of the Diels-Alder adducts ranged from 86-98% ee. The Diels-Alder adducts were easily removed from the chiral auxiliary and the latter was recyclized. The absolute and relative stereochemistry of 7 was determined from an X-ray crystal structure of the p-bromobenzoate derivative of 7. Copyright (C) 2000 Elsevier Science Ltd.