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Base‐induced cycloaddition of N ‐(tosylmethyl)imino compounds to michael acceptors. Synthesis of 2,3,4‐trisubstituted pyrroles
Author(s) -
Houwing Hendrik A.,
Van Leusen Albert M.
Publication year - 1981
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.5570180614
Subject(s) - chemistry , cycloaddition , sulfinic acid , substituent , base (topology) , medicinal chemistry , michael reaction , organic chemistry , stereochemistry , catalysis , mathematical analysis , mathematics
A series of N ‐(tosylmethyl)imino compounds [TosCH 2 NC(L)A] has been prepared, and applied to a new, base‐induced, one‐operational synthesis of otherwise more difficultly accessible 2,3,4‐trisubstituted pyrroles from electron deficient olefins. This regiospecific process probably is an 1,3‐anionic cycloaddition, combined with the elimination of sulfinic acid and a leaving group L. The group A is retained as the 2‐substituent of the resulting pyrroles.