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Enantioselective Organocatalytic Formal [3 + 3]-Cycloaddition of α,β-Unsaturated Aldehydes and Application to the Asymmetric Synthesis of (−)-Isopulegol Hydrate and (−)-Cubebaol†
| Content Provider | Semantic Scholar |
|---|---|
| Author | Bor-Cherng Tseng, And Hsing-Chang Liao, J. |
| Copyright Year | 2006 |
| Abstract | The first highly enantioselective organocatalyzed carbo [3 + 3] cascade cycloaddition of α,β-unsaturated aldehydes is reported. Using this methodology, crotonaldehyde is converted to 6-hydroxy-4-methylcyclohex-1-enecarbaldehyde, which is used in the synthesis of (−)-isopulegol hydrate, (−)-cubebaol, and p-tolualdehyde as well as (−)-6-hydroxy-4-methyl-1-cyclohexene-1-methanol acetate, an intermediate in the total synthesis of lycopodium alkaloid magellanine. Other α,β-unsaturated aldehydes give rise to chiral cyclohexadienes via formal [4 + 2] reactions. |
| Starting Page | 2217 |
| Ending Page | 2220 |
| Page Count | 4 |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/ol060486+ |
| Volume Number | 8 |
| Alternate Webpage(s) | http://www.chem.ccu.edu.tw/~bch/Publications/PubRefFiles/2006%20OL%202217-2220.pdf |
| Alternate Webpage(s) | https://doi.org/10.1021/ol060486%2B |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
