Diels-alder cycloaddition of 3-borylpropenoic acid derivatives and their use as synthetic equivalents of E-β-hydroxy acrylic acid and E-β-hydroxy vinylamine.

✍ Scribed by C. Rasset; M. Vaultier

• Book ID: 104204320
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 667 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)87019-8

✦ Synopsis

Cycloadditions of E-vinylboronic esters la-c bearing an electron withdrawing group in p position to the boronic function with 1,3-butadiene and 2,3_dimethylbutadiene give smoothly the corresponding Diels-Alder adducts. Functional group manipulations such as oxidation of the carbon-boron bond leads to the corresponding alcohol with retention of configuration. The transformation of the carboxylic acid group into an NH-Boc is possible in the presence of the botanic ester leading to tram-B-amino boronic acid derivative Sg which oxidation and deprotection give the trans-B-amino alcohol 5. This shows that 3borylpropenoic acid derivatives may be interesting synthetic equivalents of E-B-hydroxy acrylic acid and E-P-hydroxy vinylamine.