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

Authors
Sirbu, D Falck-Pederson, ML Romming, C Undheim, K
Citation
D. Sirbu et al., Palladium mediated substitutions and rearrangements in spiro[4,4]nonanes., TETRAHEDRON, 55(21), 1999, pp. 6703-6712
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
21
Year of publication
1999
Pages
6703 - 6712
Database
ISI
SICI code
0040-4020(19990521)55:21<6703:PMSARI>2.0.ZU;2-7
Abstract
The two-step NaBH4/CeCl3 1,2-reduction of spiro[4,4]nonane-2,7-diene-1,6-di one gave a trans- alcohol as a first product which reacted further to the c orresponding cis,trans-diol. Pd(II)-catalysis was used to effect an allylic rearrangement from the 1,6-diacetate to the corresponding 2,7-diacetate. B oth diacetates were substrates for Pd(0)-catalyzed allylic alkylations. The relative stereochemistry was retained. (C) 1999 Elsevier Science Ltd. All rights reserved.