Influence of aluminum Lewis acids on the diastereoselectivity of the nickel-catalyzed [2+2+2] cycloaddition of norbornadiene and electron deficient alkenes

Authors
Pardigon, O Tenaglia, A Buono, G
Citation
O. Pardigon et al., Influence of aluminum Lewis acids on the diastereoselectivity of the nickel-catalyzed [2+2+2] cycloaddition of norbornadiene and electron deficient alkenes, TETRAHEDR L, 41(21), 2000, pp. 4089-4092
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
21
Year of publication
2000
Pages
4089 - 4092
Database
ISI
SICI code
0040-4039(20000529)41:21<4089:IOALAO>2.0.ZU;2-8
Abstract
The stereoselective formation of 8-substituted deltacyclanes by homo Diels- Alder (HDA) reaction using a phosphine modified nickel catalyst generated b y reduction of Ni(acac)(2) with alkylaluminums is discussed. Depending on t he nature of the alkene and on the nickel catalytic system, fair to excelle nt exo selectivity are observed. A switch in selectivity favoring the endo- cycloadduct is observed when the polar methoxycarbonyl group substituted al kene is activated with aluminum species. (C) 2000 Elsevier Science Ltd. All rights reserved.