Journal
TETRAHEDRON LETTERS
Volume 42, Issue 3, Pages 477-479Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)01967-5
Keywords
Baylis-Hillman chemistry; regioselectivity; 2-methylenealkanoates; alkanenitriles
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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 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. (C) 2001 Elsevier Science Ltd. All rights reserved.
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