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Stereoselective addition of carbamates to unsaturated systems by means of mercury(II) nitrate. Synthesis of saturated nitrogen‐containing heterocycles
Author(s) -
Barluenga J.,
Jiménez C.,
Nájera C.,
Yus M.
Publication year - 1984
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.5570210632
Subject(s) - chemistry , sodium borohydride , mercury (programming language) , stereoselectivity , medicinal chemistry , nitrogen , intermolecular force , organic chemistry , ether , molecule , catalysis , computer science , programming language
The aminomercuration of dienes with carbamates and mercury(II) nitrate affords, after in situ demercuration with sodium borohydride, stereoselectively saturated nitrogen‐containing heterocycles. Thus, the corresponding amidomercuration‐demercuration of 1,4‐ or 1,5‐hexadiene, and diallyl ether gives respectively N ‐alkoxycarbonyl cis ‐2,5‐dimethylpyrrolidines and trans ‐3,5‐dimethylmorpholines. From 1,5‐cyclooctadiene 9‐alkoxycarbonyl‐9‐azabicyclo[3.3.1]‐ and [4.2.1]‐nonanes (molar ratio ca. 1:1) are obtained. By amidomercuration‐demercuration of N ‐allylurethane cis ‐ N,N '‐bis(ethoxycarbonyl)‐2,5‐dimethylpiperazine is obtained. The intermolecular amidomercuration of unsaturated systems results stereochemically opposite to the same aminomercuration process.