Diastereoselective spiroketalization: stereocontrol using an iron(0) tricarbonyl diene complex.
It has been demonstrated that an element of planar chirality can influence the formation of an adjacent spiroketal stereocenter. Appropriately functionalized enantiomerically pure 1- and 2-sulfinyl 1,3-dien-5-ones and their corresponding iron(0) tricarbonyl complexes (7, 17) have been prepared, and the derived spiroketals (8, 18) are made in good to excellent diastereoselectivity. A preliminary exploration of the combined effects of planar and central chirality upon the diastereoselectivity revealed matched and mismatched combinations (14).
Swarthmore College, Department of Chemistry and Biochemistry, 500 College Avenue, Swarthmore, Pennsylvania 19081, United States. rpaley1@swarthmore.edu
Robert S
RS
Paley
Madeleine C
MC
Laupheimer
Nathaniel A K
NA
Erskine
Paul R
PR
Rablen
Robert D
RD
Pike
James S
JS
Jones