Regiochemical control of the ring-opening of 1, 2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis-and trans-oxides of 4-[(benzyloxy) …

M Chini, P Crotti, LA Flippin, F Macchia…

Index: Chini, Marco; Crotti, Paolo; Flippin, Lee A.; Macchia, Franco; Pineschi, Mauro Journal of Organic Chemistry, 1992 , vol. 57, # 5 p. 1405 - 1412

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Citation Number: 25

Abstract

The synthesis of the diastereoisomeric epoxides cis-lb-d and trans-2b-d and the products of their ring-opening by various nucleophiles are described. The reaults of the ring-openings of the tmns-epoxidea 2 W can be rationaked by combining stereoelectronic and conformational arguments. However, the regioselectivity of the ring-openings of the cis-epoxides lb-d can, in principle, be influenced by the chelation of a metal ion by the oxygen atom of the epoxy ...