Cycloaddition reactions of λ-amino α,β-didehydro amino acid esters: a test case 
for the principle of 1,3-allylic strain

Reetz, Manfred T.; Kayser, Frank; Harms, Klaus

doi:10.1016/S0040-4039(00)92661-3

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Cycloaddition reactions of λ-amino α,β-didehydro amino acid esters: a test case for the principle of 1,3-allylic strain

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Reetz, Manfred T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Reetz, M. T., Kayser, F., & Harms, K. (1992). Cycloaddition reactions of λ-amino α,β-didehydro amino acid esters: a test case for the principle of 1,3-allylic strain. Tetrahedron Letters, 33(24), 3453-3456. doi:10.1016/S0040-4039(00)92661-3.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0023-CA4B-A

Abstract

N,N-Dibenzlamino aldehydes, readily accessible from amino acids, can be converted into λ-N,N-dibenzylamino α,β-didehydro amino acid esters without racemization; these undergo stereoselective Diels-Alder reactions and 1,3-dipolar cycloaddition with diazomethane, the sense of diastereoselectivity being opposite to that predicted by the conventional principle of 1,3-allylic strain