Trialkylamine versus trialkylphosphine: Catalytic conjugate addition of alcohols to alkyl propiolates
The conjugate addition of activated propargylic alcohols to alkyl propiolates is shown to be catalyst-dependent. Whereas trialkylamines catalyze the expected 1,4-adition of the alcohol on the alkynoate to give the β-alkoxyacrylate derivative, the trialkylphosphine-catalyzed reaction affords densely functionalized bicyclic hexahydrofuro[2,3-b]furan derivatives. A mechanistic proposal for the phosphine-catalyzed addition of alcohols to alkyl propiolates according with these observations is presented. © Georg Thieme Verlag Stuttgart.
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| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Published: |
Thieme
2009-04-17
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| Subjects: | Alkynes, Bicyclic compounds, phosphorus, catalysis, Amines, |
| Online Access: | http://hdl.handle.net/10261/132610 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100004587 |
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