The Baylis–Hillman chemistry in aqueous media: a convenient synthesis of 2-methylenealkanoates and alkanenitriles

✍ Scribed by Deevi Basavaiah; Nagaswamy Kumaragurubaran

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 70 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01967-5

✦ Synopsis

A convenient, general and efficient synthesis of 2-methylenealkanoates and alkanenitriles is accomplished via the regioselective nucleophilic (S N 2%) addition of hydride ion from NaBH 4 to (2Z)-2-(bromomethyl)alk-2-enoates and 2-(bromomethyl)alk-2-enenitriles respectively in the presence of DABCO in environment friendly aqueous media. Synthesis of two hypoglycemic agents is also described.