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One‐Pot synthesis of substituted pyrrolidines via aminomercuration‐demercuration of 1,4‐ and 1,5‐Hexadiene
Author(s) -
Barluenga J.,
Najera C.,
Yus 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.5570180705
Subject(s) - chemistry , stereoselectivity , yield (engineering) , intermolecular force , one pot synthesis , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , molecule , materials science , metallurgy
The aminomercuration‐demercuration of 1,4‐ and 1,5‐hexadiene yield cis‐ and trans ‐2,5‐dimethyl‐ N ‐arylpyrrolidines via one‐pot process. The intermolecular cyclization reaction goes through the corresponding mercurated pyrrolidines; these intermediates were isolated and characterized when the mercuration reaction was completed. The high stereoselectivity observed allows an easy way of synthesis for N ‐substituted trans ‐2,5‐dimethylpyrrolidines.