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2004 Organo-silicon compounds Organo-silicon compounds S 0060 Ene Cyclizations of α-(Prenyl)dialkylsilyloxy Aldehydes: Formation and Oxida- tive Cleavage of Oxasilacyclohexanols. α-silyloxy aldehydes which are generated by different routes are found to undergo stereoselective ene cyclization to oxasilacy- clohexanols. In one case formation of a siladioxolane is also observed via competing allylic transfer. The oxasilacyclohexanols smoothly undergo ring opening in the pres- ence of H 2 O 2 yielding chiral functionalized triols which are useful synthons. — (ROBERTSON*, J.; HALL, M. J.; STAFFORD, P. M.; GREEN, S. P.; Org. Biomol. Chem. 1 (2003) 21, 3758-3767; Dyson Perrins Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3QY, UK; Eng.) — Jannicke 13- 130

Ene Cyclizations of α-(Prenyl)dialkylsilyloxy Aldehydes: Formation and Oxidative Cleavage of Oxasilacyclohexanols

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Page 1: Ene Cyclizations of α-(Prenyl)dialkylsilyloxy Aldehydes: Formation and Oxidative Cleavage of Oxasilacyclohexanols

2004 Organo-silicon compounds

200413.fm Page 149 Friday, February 27, 2004 9:14 AM

Organo-silicon compoundsS 0060 Ene Cyclizations of α-(Prenyl)dialkylsilyloxy Aldehydes: Formation and Oxida-

tive Cleavage of Oxasilacyclohexanols. — α-silyloxy aldehydes which are generated by different routes are found to undergo stereoselective ene cyclization to oxasilacy-clohexanols. In one case formation of a siladioxolane is also observed via competing allylic transfer. The oxasilacyclohexanols smoothly undergo ring opening in the pres-ence of H2O2 yielding chiral functionalized triols which are useful synthons. — (ROBERTSON*, J.; HALL, M. J.; STAFFORD, P. M.; GREEN, S. P.; Org. Biomol. Chem. 1 (2003) 21, 3758-3767; Dyson Perrins Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3QY, UK; Eng.) — Jannicke

13- 130

Page 2: Ene Cyclizations of α-(Prenyl)dialkylsilyloxy Aldehydes: Formation and Oxidative Cleavage of Oxasilacyclohexanols

2004 Organo-silicon compounds

200413.fm Page 150 Friday, February 27, 2004 9:14 AM