Stereoselective synthesis of spiro-β-lactams using d-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect

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Abstract

Diastereoselective synthesis of spiro-β-lactams via [2+2] cycloaddition reaction of imines and chiral ketenes is described. The chiral ketene was prepared from commercially available, inexpensive d-glucose. Although, theoretically four diastereomers are possible, the reaction yielded only two diastereomers stereoselectively in good to moderate yields. The stereochemical outcome of the reaction was in accordance with the torquoelectronic model. © 2007 Elsevier Ltd. All rights reserved.

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Chincholkar, P. M., Puranik, V. G., & Deshmukh, A. R. A. S. (2007). Stereoselective synthesis of spiro-β-lactams using d-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect. Tetrahedron, 63(37), 9179–9187. https://doi.org/10.1016/j.tet.2007.06.073

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