Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

Tytuł:: Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.
Autorzy:: Suzuki T; Department of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.
Mate NA; Department of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.
Adhikari AA; Department of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.
Chisholm JD; Department of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.
Źródło:: Molecules (Basel, Switzerland) [Molecules] 2019 Nov 15; Vol. 24 (22). Date of Electronic Publication: 2019 Nov 15.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Original Publication: Basel, Switzerland : MDPI, c1995-
MeSH Terms:: Acetamides/*chemistry
Chloroacetates/*chemistry
Indoles/*chemistry
Lewis Acids/*chemistry
Catalysis ; Stereoisomerism
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Grant Information:: R15 GM116054 United States GM NIGMS NIH HHS; R15-GM116054 United States GM NIGMS NIH HHS; 54823-ND1 American Chemical Society Petroleum Research Fund
Contributed Indexing:: Keywords: dialkylation; indole; indolenine; spiroindoline; trichloroacetimidate
Substance Nomenclature:: 0 (Acetamides)
0 (Chloroacetates)
0 (Indoles)
0 (Lewis Acids)
I8BL3305RO (trichloroacetamide)
Entry Date(s):: Date Created: 20191117 Date Completed: 20200407 Latest Revision: 20200408
Update Code:: 20240104
PubMed Central ID:: PMC6891773
DOI:: 10.3390/molecules24224143
PMID:: 31731742
: Czasopismo naukowe

Pełny tekst

2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

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