2007

Other 6-membered heterocyclesR 0670 Singlet Oxygen Addition to Chiral Allylic Alcohols and Subsequent Peroxyacetal-

ization with β-Naphthaldehyde: Synthesis of Diastereomerically Pure 3-β-Naph-thyl-Substituted 1,2,4-Trioxanes. — The title method involves a sequence of a singlet oxygen ene reaction of allylic alcohols in dye-crosslinked polystyrene beads containing the porphyrin sensitizer, and the BF3·OEt2 catalyzed peroxyacetalization reaction of β-naphthaldehyde as model compound for aromatic carbonyl compounds with thediastereomeric mixtures of the generated β-hydroperoxy alcohols. The peroxyacetal-ization reaction affords cross-peroxyacetalization side products in each case, but these products are isolated only from the reaction mixture of cyclohexyl derivative (IId). — (GRIESBECK*, A. G.; EL-IDREESY, T. T.; LEX, J.; Tetrahedron 62 (2006) 46, 10615-10622; Inst. Org. Chem., Univ. Koeln, D-50939 Koeln, Germany; Eng.) — Klein

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