An intramolecular oxa-Michael reaction on a, beta-unsaturated alpha-amino-delta-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes

作者:Becerra-Figueroa L.; Movilla S.; Prunet J.; Miscione G. P.*; Gamba-Sanchez D.*
来源:Organic and Biomolecular Chemistry, 2018, 16(8): 1277-1286.
DOI:10.1039/c7ob03066ersc.li/obc

摘要

A highly diastereoselective intramolecular oxa-Michael reaction on alpha,beta-unsaturated alpha-aminod-delta-hydroxycarboxylic acid esters is presented; 1,3-dioxanes functionalized in positions 2,4 and 6 were obtained in good yields and with excellent selectivities; an experimental and computational study was carried out to understand the reaction course in terms of yields and selectivities. This reaction proceeds under mild reaction conditions using highly electrophilic aldehydes and ketones.

  • 出版日期2018-2-28

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