Publication: Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines of α-amino esters
Issued Date
1990-01-01
Resource Type
ISSN
00404039
Other identifier(s)
2-s2.0-0025012232
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron Letters. Vol.31, No.45 (1990), 6569-6572
Suggested Citation
Darrin A. Barr, Michael J. Dorrity, Ronald Grigg, John F. Malone, John Montgomery, Shuleewan Rajviroongit, Paul Stevenson Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines of α-amino esters. Tetrahedron Letters. Vol.31, No.45 (1990), 6569-6572. doi:10.1016/S0040-4039(00)97119-3 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/15928
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Title
Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines of α-amino esters
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Abstract
Cycloaddition of a range of imines of α-amino esters to homochiral menthyl acrylate proceeds with complete asymmetric induction at room temperature in the presence of silver(I), lithium(I) and thallium(I) salts. The imine of 2-aminomethylpyridine reacts similarly. Reversal of cycloaddition regiochemistry, together with complete asymmetric induction, occurs when titanium (IV) complexes are used as catalysts. The absolute configuration of one of the cycloadducts has been established by X-ray crystallography. © 1990.