2002 fused pyridine derivatives

fused pyridine derivativesR 0450

01 - 143Preparation of Both Enantiomers of 1-Allyl-1,2,3,4-tetrahydro-β-carboline Using Allyltin Reagents and a Chiral Auxiliary Derivedfrom L-Proline. — The first asymmetric allylation of β-carboline (I) withallyltributyltin and trichloroethyl chloroformate using a L-proline derivative aschiral auxiliary is described. When the allylation is carried out using tetraal-lyltin (V) instead of allyltributyltin (II), the stereoselectivity is reversed andthe antipode of (IV) is obtained in high yield and e.e. The formed dihydro-β-carboline is transformed via two reduction steps into the tetrahydro-β-carbolinewithout racemization. — (ITOH, TAKASHI; MATSUYA, YUJI; ENOMOTO,YASUKO; OHSAWA, AKIO; Tetrahedron 57 (2001) 34, 7277-7289; Sch. Pharm.Sci., Showa Univ., Shinagawa, Tokyo 142, Japan; EN)

1