2004 Oxirane derivatives

Oxirane derivativesR 0030 Stereospecific Synthesis of Optically Active Phenylpropylene Oxides. — It is

found that phenylpropylene oxides undergo stereospecific lithiation with sBuLi in the presence of TMEDA. Trapping of the resulting compound with different electrophiles takes place with complete retention of configuration, thus allowing the first stereospe-cific synthesis of trisubstituted phenylpropenyl oxides. Coupling with Ph-CHO pro-ceeds with low diastereoselectivity giving a mixture of syn and anti alcohols. Addition-ally, it is shown that NaBH4-mediated reduction of the keto analogue (XVI) takes place with reasonable anti selectivity. — (CAPRIATI, V.; FLORIO*, S.; LUISI, R.; NUZZO, I.; J. Org. Chem. 69 (2004) 10, 3330-3335; Dip. Farm.-Chim., Univ. Bari, I-70126 Bari, Italy; Eng.) — Jannicke

37- 103

2004 Oxirane derivatives