894415-71-5Relevant academic research and scientific papers
Enantioselective organocatalytic formal [3 + 3]-cycloaddition of α,β-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol
Hong, Bor-Cherng,Wu, Ming-Fun,Tseng, Hsing-Chang,Liao, Ju-Hsiou
, p. 2217 - 2220 (2007/10/03)
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.
