Tetrahedron Letters

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

D Basavaiah, N Kumaragurubaran

Index: Basavaiah, Deevi; Kumaragurubaran, Nagaswamy Tetrahedron Letters, 2001 , vol. 42, # 3 p. 477 - 479

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Citation Number: 59

Abstract

A convenient, general and efficient synthesis of 2-methylenealkanoates and alkanenitriles is accomplished via the regioselective nucleophilic (SN2′) addition of hydride ion from NaBH4 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.

~73%

~74%

~50%

Alkylglycidic acids: potential new hypoglycemic agents

[Ho, Winston; Tutwiler, Gene F.; Cottrell, Sandra C.; Morgans, Dave J.; Tarhan, Okan; Mohrbacher, Richard J. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2184 - 2190]