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Stereodivergent Synthesis of Substituted N,O‐Containing Bicyclic Compounds by Sequential Addition of Nucleophiles to N ‐Alkoxybicyclolactams
Author(s) -
Vincent Guillaume,
Guillot Régis,
Kouklovsky Cyrille
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201006590
Subject(s) - nucleophile , stereocenter , pyrrolidine , piperidine , metathesis , bicyclic molecule , chemistry , ring (chemistry) , yield (engineering) , stereoselectivity , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , polymer , materials science , metallurgy , polymerization
In control! N ‐alkoxybicyclolactams derived from the ring‐rearrangement metathesis of nitroso Diels–Alder cycloadducts were subjected to the successive addition of two nucleophiles to yield substituted piperidine or pyrrolidine precursors with good to excellent stereoselectivity. The relative configuration of the newly formed stereocenter can be controlled by the order of addition of the two nucleophiles.