Base‐induced cycloaddition of  N ‐(tosylmethyl)imino compounds to michael acceptors. Synthesis of 2,3,4‐trisubstituted pyrroles | Zendy

Houwing Hendrik A. | Zendy; Van Leusen Albert M. | Zendy

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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.

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