Abstract
| - The preparation of a diverse array of enantiomericallypure 1- and 2-sulfinyl dienes has beenachieved via Stille coupling of halovinyl sulfoxides and vinylstannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation ofthe corresponding sulfinyl dieneiron(0) tricarbonyl complexes was accomplished by utilizingFe(CO)5/NMO or (bda)Fe(CO)3 asiron(0)tricarbonyl transfer reagents. Installation of the iron(0)tricarbonyl fragment was shown to behighly diastereoselective (10−16:1) for(R)-(1Z)-1-sulfinyl dienes, most likely as aresult of allylic1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene isalso described.
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