@article{cca3087872894c168cd6b9949e0fdde7,
title = "3-Trimethylsilyloxy-oxetanes via a highly selective paterno-b{\"u}chi reaction",
abstract = "Benzaldehyde reacts photochemically with various trimethylsilyl enol ethers to furnish 3-trimethylsilyloxy-oxetanes in moderate to fair yields. The photocycloaddition proceeds with excellent regio- and diastereoselectivity.",
keywords = "Paterno-B{\"u}chi reaction, benzaldehyde, diastereoselectivity, oxetane, trimethylsilyl enol ether",
author = "Thorsten Bach",
note = "Funding Information: The assignment for 2c has not been definitely establisheds o far mainly due to the fact that the minor product could neitherb e isolatedn or spectroscopicallyd etected. From a simplified mechanistic point of view the reaction can be envisaged as an electrophilic attack of the photoexciteda ldehydeat the electron rich alkene which leads to formation of the O-C bond. The intermediate biradical collapses to the final product or it cleaves back to the startingm aterials.T his model which is basedo n the thoroughi nvestigationsb y Freilich and Peters13e nablest o explain both the regio-and stereoselectivityo f the reaction. Obviously the ring closure occurs preferentially such that the two large substitue.nts(P henyl and R) approache ach other in an anti-manner. We believe that the described selectiver oute to 3-trimethylsilyloxy-oxetanesw ill be of grearv alue for the con-structiono f complex carbon skeletons.O ur efforts are currently devotedt o the extension of this method to other silylenolethersa nd aldehydesa nd its applicationt o naturalp roducts ynthesis. Acknowledgments: Support of this work by the Fonds der ChemischenI ndustrie and the Sti.ftungV olkswagen-werk (KekulC fellowship) is gratefully acknowledged. I would like to thank Prof. M.T. Reetz for many valuable and stimulatingd iscussionsa nd R. Weber for skillful technicala ssistance.",
year = "1991",
month = nov,
day = "25",
doi = "10.1016/0040-4039(91)85033-2",
language = "English",
volume = "32",
pages = "7037--7038",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Ltd.",
number = "48",
}