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• W1559978033 abstract "Abstract The chemical reactivity encoded in a highly substituted cyclobutane platform, which contains the ( E , E )‐dimethyl 2,2′‐(cyclobutane‐1,2‐diylidene)diacetate structural motif, has been explored. The cyclobutane platform features a C 2 axis of symmetry as well as a dense and interconnected ring functionalization pattern that is defined by two allylic/benzylic stereogenic oxygen‐containing quaternary centers with a 1,2‐ trans configuration and two exocyclic acrylate chains. The reactivity profile of the cyclobutane platform is defined by two important kinetic barriers (steric strain and antiaromaticity) and two structure‐biased chemical processes: (1) the thermally‐driven [3,3] sigmatropic rearrangement between one of the two equivalent aryloates and the corresponding allylic acrylate chain and (2) the allylic nucleophilic substitution (S N 2′ reaction) that involves a tertiary aryloate and its exocyclic double bond (anti‐Michael addition). The reaction of platform 3a with secondary amines delivered the corresponding cyclobutene amino acid derivatives 15a – 15f in excellent yields (up to ≥95 %) and high diastereoselectivities (up to 99:1). Computational studies are described to rationalize the observed diastereoselectivity." @default.
• W1559978033 created "2016-06-24" @default.
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• W1559978033 date "2015-04-20" @default.
• W1559978033 modified "2023-10-10" @default.
• W1559978033 title "Hydrogen Bond Controlled Anti-Aza-Michael Addition: Diastereoselective Synthesis of Cyclobutene-Containing Amino Acid Derivatives" @default.
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• W1559978033 doi "https://doi.org/10.1002/ejoc.201500269" @default.
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