B. Breit, S. Zahn
Apr 2, 1998
Citations
0
Influential Citations
24
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The hydroformylation of 2-phenyl-4-(prop-2-enyl)[1,3]dioxanes has been studied. anti -Acetals 1a,b were found to give extraordinarily high diastereoselectivity on hydroformylation, giving rise to the formation of the all- anti stereotriades 2a,b . The origin of this stereoselectivity may be related to the preferred conformation of the actetals 3 in solution, as determined by 2D-NOESY NMR experiments and force field calculations (MM3). Hydroformylation of 1a afforded an intermediate for a short and efficient synthesis of a key building block for the total synthesis of the macrolide antibiotic bafilomycin A 1 .