Sulfinyl-mediated stereoselective Overman rearrangements and Diels-Alder cycloadditions.
The Overman rearrangement of allylic sulfinyl trichloroacetimidates affords sulfinyl trichloroacetamides with high stereoselectivity and excellent yields. Bis-allylic substrates lead to amido 2-sulfinyl butadiene derivatives in excellent yields, with total chemo- and diastereoselectivity. The Diels-Alder cycloaddition of related dienes is controlled by the sulfoxide moiety.
Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es
Roberto
R
Fernández de la Pradilla
Ignacio
I
Colomer
Alma
A
Viso
D003500:Cyclization; D015394:Molecular Structure; D012451:Safrole / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D013457:Sulfur Compounds; D012451:Safrole; C005746:sulfoxide