A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
The base-promoted Michael–aldol anionic domino reactions of cyclic α-nitro ketones and α,β-unsaturated aldehydes afforded bicyclo[n.3.1]alkanone systems of seven different ring sizes (n = 3–9), normally in excellent yields. This can be considered the first general method for the synthesis of this ty...
| Authors: | ; ; ; ; |
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| Format: | Article |
| Publication date: | 2011 |
| Country: | España |
| Institution: | Universidad Complutense de Madrid (UCM) |
| Repository: | Docta Complutense |
| Language: | English |
| OAI Identifier: | oai:docta.ucm.es:20.500.14352/128700 |
| Online Access: | https://hdl.handle.net/20.500.14352/128700 |
| Access Level: | Open access |
| Keyword: | 547 Bicyclic compounds Domino reactions Michael addition Aldol reactions Diastereoselectivity Química orgánica (Química) 2306.04 Química de Los Compuestos Bicíclicos |
| Summary: | The base-promoted Michael–aldol anionic domino reactions of cyclic α-nitro ketones and α,β-unsaturated aldehydes afforded bicyclo[n.3.1]alkanone systems of seven different ring sizes (n = 3–9), normally in excellent yields. This can be considered the first general method for the synthesis of this type of carbocycle. Furthermore, up to four stereocentres are generated, three of which are contiguous and include a functionalized quaternary bridgehead carbon atom. The diastereoselectivity was often complete, was much higher than in les general reactions based on related domino processes, and involved the generation of a different major diastereomer due to the control of the Michael and aldol individual steps of the reaction by the nitro group |
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