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Synthesis 2018; 50(03): 599-606
DOI: 10.1055/s-0036-1591493
DOI: 10.1055/s-0036-1591493
paper
Controlled and Efficient Stereoselective Synthesis of Oxindole-Appended 1-Aza-1,3-butadiene Derivatives via a One-Pot Buchwald–Hartwig Amination/Elimination Strategy
We gratefully acknowledge the financial assistance from DST-Fast Track Young Scientist Award (Ref. No. CS/FT95/2014) and SERB-EMEQ (Ref. No. SB-EMEQ-297/2014).Further Information
Publication History
Received: 18 September 2017
Accepted after revision: 21 September 2017
Publication Date:
12 October 2017 (online)
Abstract
The enamine-free, stereoselective synthesis of oxindole-appended 1-aza-1,3-butadienes with an electron-withdrawing-group at the 3-position has been achieved in good yields from (Z)-β-bromo-substituted Morita–Baylis–Hillman (MBH) adducts of oxindoles via a one-pot Buchwald–Hartwig amination/elimination strategy. The versatility of the (Z)-β-bromo MBH adducts of oxindoles was further demonstrated by the formation of π-conjugated oxindole derivatives in typical palladium-catalysed coupling reactions.
Key words
Buchwald–Hartwig amination - β-bromo Morita–Baylis–Hillman adducts - halo aldol reaction - oxindole-appended 1-aza-1,3-butadienes - eliminationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591493.
- Supporting Information
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