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Author(s): Ali A; Gill GB; Pattenden G; Roan GA; Kam TS
Title: Palladium-and cobalt-mediated cyclisations of halo-polyenes: A comparative study
Source: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (11): 1081-1093
Date: 1996 JUN 7
Document Type: Journal : Article
DOI:
Language: English
Comment:
Address: UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND.
Reprint:
E-mail:
Author Keywords:
KeyWords Plus: FREE-RADICAL CYCLIZATIONS; 3-DEOXY-D-MANNO-2-OCTULOSONATE AMMONIUM KDO;
CATALYTIC ASYMMETRIC-SYNTHESIS; ACYLCOBALT SALOPHEN REAGENTS; BOND-
FORMING REACTIONS; CARBON CENTERS; HYDROCOBALTATION REACTIONS;
FUNCTIONALIZED ALKENES; ALKYLCOBALT COMPLEXES; ORGANIC-SYNTHESIS
Abstract: Cobalt(I)-mediated mono-and bi-cyclisations of halo-polyenes are compared and contrasted with corresponding reactions using the Heck reaction. The procedures are found to complement one another, with each having advantages and disadvantages, in the cases studied. Thus, treatment of the vinyl iodide 1 under Heck conditions led to the novel 1,3-diene 3 in 93% yield, whereas reaction between 1 and cobalt(I) salophen resulted in the formation of the organocobalt complex 4 (similar to 50%) as black crystals. Subsequent irradiation of 4 then led to the 6,5-ring fused bicycle 5 in 85% yield. In similar fashion, a Heck reaction with the analogous vinyl iodide 8 produced the product 9 of 6-ring cyclisation followed by beta-hydride elimination, whereas the corresponding cobalt-mediated reaction with 8 led to the new organocobalt 10 albeit in only low yield (similar to 20%). In reactions akin to those studied by Overman et al., Heck reaction with the dienyl aryl iodide 14 was shown to lead to a mixture of the bicycle 16 and the tricycle 17 in a 1:1 ratio. By contrast treatment of 14 with cobalt(I) salophen produced largely the tetralin 18. The iodo-diene 33 gave rise to the spirocycle 35 under Heck reaction conditions, and the related spirocycle 42 was produced from the bromo-acetal 40 via 41, using cobalt(I) mediated reactions.
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