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 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.
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
Bin
B
Tan
Di
D
Zhu
Lihong
L
Zhang
Pei Juan
PJ
Chua
Xiaofei
X
Zeng
Guofu
G
Zhong
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D000475:Alkenes; D012997:Solvents; D013764:Tetrahydronaphthalenes; D014867:Water