Abstract
A highly diastereoselective one-pot tandem Michael-Michael addition reaction developed in a rotamerically locked conformation is described. Reaction of isocyanates 8 – 13 with hydroxylactone 14 gave tandem Michael-Michael adducts 22 – 26 in good to excellent yields. The intermediate tricyclic oxazolidinones consisted of rotamer pairs 16 – 19, and the rotation barriers of some of these compounds were determined. The tandem addition reaction was highly accelerated by introducing conformation anchoring group X. A new versatile synthesis of octahydroacridines 27 – 29 using the tandem adducts is also described.
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