36784-73-3

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 64-19-7 acetic acid 
• 123-31-9 hydroquinone 
• 91056-61-0 2-Ethoxy-4-methyl-1,2,5,6-tetrahydrobenzaldehyd 
• 17466-13-6 1-ethoxy-3-methyl-buta-1,3-diene 
• 58274-64-9 trimethyl[(3-methylbuta-1,3-dien-1-yl)oxy]silane 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 107-02-8 acrolein 
• 86778-42-9 4-Methyl-2-trimethylsilanyloxy-cyclohex-3-enecarbaldehyde 

Relevant 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

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.

CHEMISTRY OF ENOL ETHERS. LXII. DIENE CONDENSATION OF 1-TRIMETHYLSILYLOXY-1,3-DIENES WITH α,β-UNSATURATED ALDEHYDES

The diene condensation of 1-trimethylsilyloxy-1,3-dienes (1-trimethylsilyloxy-1,3-butadiene, 1-trimethylsilyloxy-2-methyl-1,3-pentadiene, 1-trimethylsilyloxy-3-methyl-1,3-butadiene) with α,β-unsaturated aldehydes (acrylic, crotonic) is regioselective, leading to the formation of the "ortho isomers," and the cis-adducts are obtained preferentially.When heated with 10percent hydrochloric acid, the mono- and dimethyl-substituted 1-formyl-2-trimethylsilyloxy-3-cyclohexenes obtained during the diene condensation give high yields of the corresponding substituted 1-formyl-1,3-cyclohexadienes.