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Intramolecular Metalloamination of N , N ‐Dimethylhydrazinoalkenes: A Versatile Method to Access Functionalized Piperidines and Pyrrolidines
Author(s) -
Sunsdahl Bryce,
Smith Adrian R.,
Livinghouse Tom
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407768
Subject(s) - diethylzinc , chemistry , intramolecular force , acylation , zinc , combinatorial chemistry , reaction conditions , organic chemistry , catalysis , enantioselective synthesis
Highly diastereoselective metalloamination/cyclization reactions of zinc(II) hydrazides obtained through reaction of diethylzinc with N , N ‐dimethylhydrazinoalkenes are described. The resulting organozinc intermediates undergo facile allylation and acylation, in situ, to provide the corresponding functionalized piperidines and pyrrolidines.
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