Stereoselective electrophile-induced mono- and bis-cyclisation-fragmentation reactions of alkenyl oxime O-allyl and O-benzyl ethers. Synthesis of dihydropinidine

DÖNDAŞ, HACI; Grigg, R; Markandu, J; Perrior, T; Suzuki, T; Thibault, S; Thomas, WA; Thornton-Pett, M

doi:10.1016/s0040-4020(01)01118-8

Stereoselective electrophile-induced mono- and bis-cyclisation-fragmentation reactions of alkenyl oxime O-allyl and O-benzyl ethers. Synthesis of dihydropinidine

DÖNDAŞ H. A., Grigg R., Markandu J., Perrior T., Suzuki T., Thibault S., ...Daha Fazla

TETRAHEDRON, cilt.58, sa.1, ss.161-173, 2002 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 58 Sayı: 1
Basım Tarihi: 2002
Doi Numarası: 10.1016/s0040-4020(01)01118-8
Dergi Adı: TETRAHEDRON
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.161-173
Çukurova Üniversitesi Adresli: Hayır

Özet

Phenylseleny bromide-induced cyclisation of gamma- and delta-unsaturated aldoxime and ketoxime O-allyl and O-benzyl ethers is followed by a slow fragmentation of the resultant oxyiminium ions furnishing cyclic iminium salts which are readily reduced to pyrrolidines, piperidines or tetrahydroisoquinolines by sodium borohydride; dialkenyl oximes yield indolizidines and quinolizidines by an analogous sequence terminating in a mercury(II)-induced cyclisation. (C) 2002 Elsevier Science Ltd. All rights reserved.