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

Research output: Contribution to journalArticleResearchpeer-review

14 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

Cite this

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title = "Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones",
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.",
keywords = "Enantioselectivity, stereogenic centers, Isatin",
author = "Dewi Susanti and Ng, {Linda Li Ru} and Chan, {Philip Wai Hong}",
year = "2014",
doi = "10.1002/adsc.201300911",
language = "English",
volume = "356",
pages = "353 -- 358",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",
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}

Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones. / Susanti, Dewi; Ng, Linda Li Ru; Chan, Philip Wai Hong.

In: Advanced Synthesis and Catalysis, Vol. 356, No. 2-3, 2014, p. 353 - 358.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones

AU - Susanti, Dewi

AU - Ng, Linda Li Ru

AU - Chan, Philip Wai Hong

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - Enantioselectivity

KW - stereogenic centers

KW - Isatin

U2 - 10.1002/adsc.201300911

DO - 10.1002/adsc.201300911

M3 - Article

VL - 356

SP - 353

EP - 358

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 2-3

ER -