Thia-acyliminium-olefin cyclizations

JAM Hamersma, WN Speckamp

Index: Hamersma, J. A. M.; Speckamp, W. N. Tetrahedron, 1982 , vol. 38, # 22 p. 3255 - 3266

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Citation Number: 18

Abstract

Regioselective NaBH4/H+-reduction of thiazolidinediones 3-8 substituted at the nitrogen atom with different π-nucleophiles affords hydroxylactams 9-14 in good yields. The latter compounds are excellent precursors for the α-acyliminium ion 16 and can be stereoselectively cyclized in HCOOH to yield novel heterocyclic ring systems of varied structures. Because of the stereoelectronic control in the ring closure stereoselective ...