Synthesis and Diastereoselective Complexation of Enantiopure Sulfinyl Dienes:  The Preparation of Sulfinyl Iron(0) Dienes

The preparation of a diverse array of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via Stille coupling of halovinyl sulfoxides and vinyl stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of the corresponding sulfinyl diene iron...

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Bibliographic Details
Published in:Journal of organic chemistry 1997-09, Vol.62 (18), p.6326-6343
Main Authors: Paley, Robert S, de Dios, Alfonso, Estroff, Lara A, Lafontaine, Jennifer A, Montero, Carlos, McCulley, David J, Rubio, M. Belén, Ventura, Maria Paz, Weers, Heather L, Fernández de la Pradilla, Roberto, Castro, Sonia, Dorado, Rocío, Morente, Miguel
Format: Article
Language:English
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Summary:The preparation of a diverse array of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via Stille coupling of halovinyl sulfoxides and vinyl stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of the corresponding sulfinyl diene iron(0) tricarbonyl complexes was accomplished by utilizing Fe(CO)5/NMO or (bda)Fe(CO)3 as iron(0) tricarbonyl transfer reagents. Installation of the iron(0) tricarbonyl fragment was shown to be highly diastereoselective (10−16:1) for (R)-(1Z)-1-sulfinyl dienes, most likely as a result of allylic 1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene is also described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo970693a