Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones

Dewi Susanti, Linda Li Ru Ng, Philip Wai Hong Chan

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17 Citations (Scopus)

Abstract

2-Alkylaminophenylprop-1-yn-3-ols, pre-pared from the lithium diisopropylamide (LDA)-mediated 1,2-addition of alkynes to 1-(2-amino-phenyl) ketones, can be converted to 3,3-disubstituted 2-oxindoles by using silica gel inn-hexane/ethyl acetate (20:1 v/v) as the reaction medium.The utility of the approach as a potential scale-up strategy for the synthesis of 2-oxindoles was exemplified by the large-scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.
Original languageEnglish
Pages (from-to)353 - 358
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number2-3
DOIs
Publication statusPublished - 2014
Externally publishedYes

Keywords

  • Enantioselectivity
  • stereogenic centers
  • Isatin

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