Palladium catalyzed cyclizations of enantiomerically pure acyclic 4-acetoxy-2,8-nonadienes: efficient chirality transfer

Von Oppolzer, Wolfgang; Birkinshaw, Timothy Nicholas; Bernardinelli, Gérald Hugues

doi:10.1016/S0040-4039(00)97225-3

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Palladium catalyzed cyclizations of enantiomerically pure acyclic 4-acetoxy-2,8-nonadienes: efficient chirality transfer

Contributeurs/tricesVon Oppolzer, Wolfgang; Birkinshaw, Timothy Nicholas; Bernardinelli, Gérald Hugues

Publié dansTetrahedron Letters, vol. 31, no. 48, p. 6995-6998

Date de publication1990

Résumé

S-4-Acetoxy-6-aza-2,8-nonadienes 9 and 11 were subjected to Pd(0)-catalyzed cyclizations. The S,E-acetate 9 gave exclusively S,E-pyrrolidine 12, whereas the antipodal product R,E-12 was formed from the S,Z-precursor 11 (Scheme 3). X-ray-diffraction analysis of tartrate 13 served to assign the absolute configuration of 12.

Structure d'affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (format ISO)

VON OPPOLZER, Wolfgang, BIRKINSHAW, Timothy Nicholas, BERNARDINELLI, Gérald Hugues. Palladium catalyzed cyclizations of enantiomerically pure acyclic 4-acetoxy-2,8-nonadienes: efficient chirality transfer. In: Tetrahedron Letters, 1990, vol. 31, n° 48, p. 6995–6998. doi: 10.1016/S0040-4039(00)97225-3

Article (Published version)

Identifiants

PID : unige:152791
DOI : 10.1016/S0040-4039(00)97225-3

URL commercialhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900972253

ISSN du journal0040-4039

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Palladium catalyzed cyclizations of enantiomerically pure acyclic 4-acetoxy-2,8-nonadienes: efficient chirality transfer

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