Unusual Rearrangement of Spiro β-Lactams to 1,4-Diazabicyclo[4,4,0]decanes and...

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2003 Pyrazine derivatives Pyrazine derivatives R 0550 Unusual Rearrangement of Spiro β-Lactams to 1,4-Diazabicyclo[4,4,0]decanes and 1,4-Diazabicyclo[4,3,0]nonanes. Synthesis of Conformationally Restricted σ-Receptor Ligands. — Easily prepared bicyclic aldehydes (III) undergo an unusual rearrangement during catalytic hydrogenation giving diazabicycloalkanones (IV) in excellent yields. The rearrangement of analogous chiral aldehydes occurs with com- plete loss of chirality. — (MACIAS, A.; ALONSO, E.; DEL POZO*, C.; GONZALEZ, J.; Tetrahedron Lett. 45 (2004) 24, 4657-4660; Dep. Quim. Org. Inorg., Fac. Quim., Univ. Oviedo, E-33071 Oviedo, Spain; Eng.) — Mais 38- 167

Transcript of Unusual Rearrangement of Spiro β-Lactams to 1,4-Diazabicyclo[4,4,0]decanes and...

Page 1: Unusual Rearrangement of Spiro β-Lactams to 1,4-Diazabicyclo[4,4,0]decanes and 1,4-Diazabicyclo[4,3,0]nonanes. Synthesis of Conformationally Restricted σ-Receptor Ligands.

2003 Pyrazine derivatives

Pyrazine derivativesR 0550 Unusual Rearrangement of Spiro β-Lactams to 1,4-Diazabicyclo[4,4,0]decanes

and 1,4-Diazabicyclo[4,3,0]nonanes. Synthesis of Conformationally Restricted σ-Receptor Ligands. — Easily prepared bicyclic aldehydes (III) undergo an unusual rearrangement during catalytic hydrogenation giving diazabicycloalkanones (IV) in excellent yields. The rearrangement of analogous chiral aldehydes occurs with com-plete loss of chirality. — (MACIAS, A.; ALONSO, E.; DEL POZO*, C.; GONZALEZ, J.; Tetrahedron Lett. 45 (2004) 24, 4657-4660; Dep. Quim. Org. Inorg., Fac. Quim., Univ. Oviedo, E-33071 Oviedo, Spain; Eng.) — Mais

38- 167