Sequential Michael Addition/Electrophilic Alkynylation: Synthesis of α-Alkynyl-ß-Substituted Ketones and Chromanones.
J Org Chem
; 83(21): 13604-13611, 2018 11 02.
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| ID: mdl-30284445
ABSTRACT
We describe the synthesis of α-alkynyl-ß-substituted cyclic ketones and analogue chromanones via one-pot Michael addition/hypervalent iodine-based α-alkynylation. Cu(I)-catalyzed Michael addition using either alkyl-aluminum or Grignard reagents, followed by diastereoselective electrophilic alkynylation of the resulting enolate by 1-ethynyl-1λ3,2-benziodoxol-3(1H)-one (EBX) resulted in the α-alkynyl-ß-substituted cyclic ketones or chromanones within 34-89% yield (16 examples). The reaction was successfully upscaled to the 5 mmol scale, and further functionalization of a model alkynylated ketone was demonstrated.
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MEDLINE
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J Org Chem
Año:
2018
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Article