Palladium mediated substitutions and rearrangements in spiro[4,4]nonanes

Autor: Kjell Undheim, Doina Sirbu, Mette Lene Falck-Pedersen, Christian Rømming
Rok vydání: 1999
Předmět:
Zdroj: Tetrahedron. 55:6703-6712
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00316-6
Popis: The two-step NaBH 4 CeCl 3 1,2-reduction of spiro[4,4]nonane-2,7-diene-1,6-dione gave a rans-alcohol as a first product which reacted further to the corresponding cis,trans-diol. Pd(II)-catalysis was used to effect an allylic rearrangement from the 1,6-diacetate to the corresponding 2,7-diacetate. Both diacetates were substrates for Pd(0)-catalyzed allylic alkylations. The relative stereochemistry was retained.
Databáze: OpenAIRE