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Iodocyclization Reactions for the Desymmetrization of Cyclohexa-1,4-dienes

✍ Scribed by Butters, M.; Elliott, M. C.; Hill-Cousins, J.; Paine, J. S.; Walker, J. K. E.

Book ID: 127278745
Publisher: American Chemical Society
Year: 2007
Tongue: English
Weight: 86 KB
Volume: 9
Category: Article
ISSN: 1523-7060
DOI: 10.1021/ol701492g

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ChemInform Abstract: An Improved Protocol for the Prins Desymmetrization of Cyclohexa-1,4-dienes.

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A straightforward route to polyols, amino polyols, polysubstituted lactols and lactones from readily available arenes has been devised. It uses a three-or four-step sequence involving a Birch reduction of the arene, followed by desymmetrization through dihydroxylation or aminohydroxylation and, last

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## Abstract The Prins cyclisation has been used for the first time to desymmetrise a 1,4‐diene. Products derived from both normal Prins and rearrangement pathways were obtained, all with complete stereocontrol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)