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2004
Oxirane derivatives
R 0030
Convergent Synthesis of cis-α,β-Epoxy-carboxylic Acids from 1-Halo-2-trimeth— A wide variety of aldehydes are trans50- 063 ylsilyloxy-3-aza-4-phenyl-1,3-butadiene.
formed into diastereomeric mixtures of oxazines via 2-azadienes like (III). The
N-Boc-protected analogues are converted into the desired cis-epoxides by a one-pot
two-step sequence involving ring opening and nucleophilic substitution of the halogen
atom resulting in the final formation of the oxirane ring. Starting from oxazines (VII)
or (VIII), almost the same diastereomeric ratios of the epoxides are obtained, thus
allowing to apply mixtures of protected substrates. — (PANUNZIO*, M.; BONGINI,
A.; MONARI, M.; TAMANINI, E.; BANDINI, E.; Tetrahedron 60 (2004) 38,
8347-8356; Dip. Chim. "G. Ciamician", Univ. Bologna, I-40126 Bologna, Italy; Eng.)
— Klein
2004
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