Tetrahedron letters

N-Acyl-2-benzoxazolinones in titanium-mediated aldol reactions

MA Burlingame, E Mendoza, GW Ashley

Index: Burlingame, Mark A.; Mendoza, Esteban; Ashley, Gary W. Tetrahedron Letters, 2004 , vol. 45, # 14 p. 2961 - 2964

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Citation Number: 13

Abstract

N-Acyl-2-benzoxazolinones readily form trichlorotitanium enolates that react rapidly with aldehydes to provide crystalline syn-aldol adducts in high yield. The resulting products are simply converted to amides, esters, and thioesters. A simple, economical synthesis of 3- hydroxy-2-methylpentanoate N-propionylcysteamine thioesters based on these findings is presented.