X=Y-ZH systems as potential 1.3-dipoles. Part 14.1 1 Part 13, R. Grigg, M. Dowling, M.W. Jordan, J. Kemp and V. Sridharan, Tetrahedron, submitted. bronsted and Lewis acid catalysis of cycloadditions of arylidene imines of α-amino acid esters

Ronald Grigg; H. Q.Nimal Gunaratne; Visuvanathar Sridharan

doi:10.1016/S0040-4020(01)87794-2

X=Y-ZH systems as potential 1.3-dipoles. Part 14.¹ 1 Part 13, R. Grigg, M. Dowling, M.W. Jordan, J. Kemp and V. Sridharan, Tetrahedron, submitted. bronsted and Lewis acid catalysis of cycloadditions of arylidene imines of α-amino acid esters

Ronald Grigg^*, H. Q.Nimal Gunaratne, Visuvanathar Sridharan

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

47 Citations (Scopus)

Abstract

Cycloadditions of arylidene imines of α-amino acid esters to a range of dipolarophiles show substantial rate enhancements in the presence of Bronsted and Lewis acids. For Bronsted acids the rate is related to the pK_a of the acid and cycloadditions to reactive dipolarophiles occur at room temperature. For the Lewis acids studied the rate acceleration decreases in the order Zn(OAc)₂ > AgOAc > LiOAc > MgOAc₂ but is also anion dependent with LiBr > LiOAc and AgOAc > AgOTs. The Lewis acid catalysed processes are believed to be examples of cycloadditions of metallo-1,3-dipoles. In both Bronsted and Lewis acid catalysed processes the cycloadditions are regio- and stereo-specific.

Original language	English
Pages (from-to)	5887-5898
Number of pages	12
Journal	Tetrahedron
Volume	43
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4020(01)87794-2
Publication status	Published - 1987

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Grigg, R., Gunaratne, H. Q. N., & Sridharan, V. (1987). X=Y-ZH systems as potential 1.3-dipoles. Part 14.¹ 1 Part 13, R. Grigg, M. Dowling, M.W. Jordan, J. Kemp and V. Sridharan, Tetrahedron, submitted. bronsted and Lewis acid catalysis of cycloadditions of arylidene imines of α-amino acid esters. Tetrahedron, 43(24), 5887-5898. https://doi.org/10.1016/S0040-4020(01)87794-2

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title = "X=Y-ZH systems as potential 1.3-dipoles. Part 14.1 1 Part 13, R. Grigg, M. Dowling, M.W. Jordan, J. Kemp and V. Sridharan, Tetrahedron, submitted. bronsted and Lewis acid catalysis of cycloadditions of arylidene imines of α-amino acid esters",

abstract = "Cycloadditions of arylidene imines of α-amino acid esters to a range of dipolarophiles show substantial rate enhancements in the presence of Bronsted and Lewis acids. For Bronsted acids the rate is related to the pKa of the acid and cycloadditions to reactive dipolarophiles occur at room temperature. For the Lewis acids studied the rate acceleration decreases in the order Zn(OAc)2 > AgOAc > LiOAc > MgOAc2 but is also anion dependent with LiBr > LiOAc and AgOAc > AgOTs. The Lewis acid catalysed processes are believed to be examples of cycloadditions of metallo-1,3-dipoles. In both Bronsted and Lewis acid catalysed processes the cycloadditions are regio- and stereo-specific.",

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Grigg, R, Gunaratne, HQN & Sridharan, V 1987, 'X=Y-ZH systems as potential 1.3-dipoles. Part 14.¹ 1 Part 13, R. Grigg, M. Dowling, M.W. Jordan, J. Kemp and V. Sridharan, Tetrahedron, submitted. bronsted and Lewis acid catalysis of cycloadditions of arylidene imines of α-amino acid esters', Tetrahedron, vol. 43, no. 24, pp. 5887-5898. https://doi.org/10.1016/S0040-4020(01)87794-2

X=Y-ZH systems as potential 1.3-dipoles. Part 14.¹ 1 Part 13, R. Grigg, M. Dowling, M.W. Jordan, J. Kemp and V. Sridharan, Tetrahedron, submitted. bronsted and Lewis acid catalysis of cycloadditions of arylidene imines of α-amino acid esters. / Grigg, Ronald; Gunaratne, H. Q.Nimal; Sridharan, Visuvanathar.
In: Tetrahedron, Vol. 43, No. 24, 1987, p. 5887-5898.

Research output: Contribution to journal › Article › peer-review

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