Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives

Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-alpha -pinene I resulted in enantiomerically pure beta -lactams 2, whi ch were converted to enantiomeric beta -amino esters 3 and 1,3-amino alcoho ls 4 and 6 with ee >99%. The resulting 1,3-difunctional compounds 3, 4 and 6 were transformed to fused saturated 1,3-heterocycles such as tetrahydro-1 ,3-oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin-4-one 13 enantiomers. (C) 2000 Elsevier Science Ltd. All rights reserved.