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Metalated Nitriles: S N i and S N i′ Installation of Contiguous Quaternary–Tertiary and Quaternary–Quaternary Centers
Author(s) -
LujanMontelongo Jesus A.,
Lu Ping,
Liu Wang,
Fleming Fraser F.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301046
Subject(s) - quaternary , stereocenter , computer science , chemistry , geology , paleontology , enantioselective synthesis , catalysis , biochemistry
“Black belt” S N i and S N i′ : Deuterium labeling revealed an inherent preference of N‐ and C‐ metalated nitriles for S N i, rather than S N i′ displacement. The fundamental reactivity preferences are harnessed in a series of cyclizations to cis‐ and trans‐ decalins that install contiguous quaternary–tertiary and quaternary–quaternary stereocenters (see scheme).