Water-More Than Just a Green Solvent: A Stereoselective One-Pot Access to All-Chiral Tetrahydronaphthalenes in Aqueous Media

A facile and highly stereoselective construction of heavily functionalized chiral tetrahydronaphthalene skeletons fused with an oxazolidine moiety has been developed The process involves an organocatalytic tandem Michael/nitrone formation/intramolecular [3+2] nitrone-olefin cycloaddition in aqueous media Using rationally designed substrates, the reacnon conditions have been optimized and the one-pot process has been applied to a series of nitroolefin acrylates and aldehydes. The N-hydroxyphenylamine component used in the second step has also been varied The stereochemistry of one product has been verified by an X-ray crystal structure determination The water used in the strategy not only constitutes an environmentally benign solvent, but also helps to improve the reactivity and stereoselectivity.