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First synthesis of chiral 3‐vinylindoles as 4π‐components for diels‐alder reactions
Author(s) -
Pindur Ulf,
Lutz Gundula,
Rogge Martina
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320133
Subject(s) - chemistry , reactivity (psychology) , sulfoxide , organic chemistry , diels–alder reaction , wittig reaction , medicinal chemistry , catalysis , alternative medicine , pathology , medicine
The first syntheses of chiral 3‐ and 2‐vinylindoles bearing sulfoxide or (‐)‐menthyloxy functional groups at the β‐vinyl positions by way of procedures based on the Horner‐Wadsworth‐Emmons and Wittig reactions, respectively, are described. Some Diels‐Alder reactions demonstrating the 4π‐reactivity of these compounds are reported.