S. Lait, M. Parvez, B. Keay
Mar 21, 2003
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-1-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels–Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5.