Diastereoselective Spiroketalization: Stereocontrol Using An Iron(0) Tricarbonyl Diene Complex
Document Type
Article
Publication Date
1-7-2011
Published In
Organic Letters
Abstract
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).
Recommended Citation
Robert S. Paley; Madeleine Claire Laupheimer , '10; Nathaniel A. K. Erskine , '10; Paul R. Rablen; R. D. Pike; and J. S. Jones.
(2011).
"Diastereoselective Spiroketalization: Stereocontrol Using An Iron(0) Tricarbonyl Diene Complex".
Organic Letters.
Volume 13,
Issue 1.
58-61.
DOI: 10.1021/ol102472g
https://works.swarthmore.edu/fac-chemistry/69