1227182-14-0Relevant articles and documents
Water-more than just a green solvent: a stereoselective one-pot access to all-chiral tetrahydronaphthalenes in aqueous media
Tan, Bin,Zhu, Di,Zhang, Lihong,Chua, Pei Juan,Zeng, Xiaofei,Zhong, Guofu
experimental part, p. 3842 - 3848 (2010/07/05)
A facile and highly stereose-lective construction of heavily function-alized chiral tetrahydronaphthalene skeletons fused with an oxazolidine moiety has been developed. The pro-cess involves an organocatalytic tandem Michael/nitrone formation/in-tramolecular [3+2] nitrone-olefin cy-cloaddition in aqueous media. Using rationally designed substrates, the reaction conditions have been optimized and the one-pot process has been ap-plied to a series of nitroolefin acrylates and aldehydes. The N-hydroxyphenyla-mine component used in the second step has also been varied. The stereo-chemistry of one product has been verified by an X-ray crystal structure determination. The water used in the strategy not only constitutes an envi-ronmentally benign solvent, but also helps to improve the reactivity and ste-reoselectivity.