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Water—More Than Just a Green Solvent: A Stereoselective One‐Pot Access to All‐Chiral Tetrahydronaphthalenes in Aqueous Media
Author(s) -
Tan Bin,
Zhu Di,
Zhang Lihong,
Chua Pei Juan,
Zeng Xiaofei,
Zhong Guofu
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902932
Subject(s) - stereoselectivity , aqueous medium , aqueous solution , solvent , chemistry , chemical engineering , organic chemistry , catalysis , engineering
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 reaction 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.