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Enantioselective Alkylation of 2‐Oxindoles Catalyzed by a Bifunctional Phase‐Transfer Catalyst: Synthesis of (−)‐Debromoflustramine B
Author(s) -
Craig Ryan,
Sorrentino Emiliano,
Con Stephen J.
Publication year - 2018
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.201800313
Subject(s) - enantioselective synthesis , bifunctional , stereocenter , alkylation , oxindole , catalysis , combinatorial chemistry , chemistry , yield (engineering) , organic chemistry , substrate (aquarium) , materials science , metallurgy , oceanography , geology
A new bifunctional phase‐transfer catalyst that employs hydrogen bonding as a control element was developed to promote efficient enantioselective S N 2 reactions for the construction all‐carbon quaternary stereocenters in high yield and excellent enantioselectivity (up to 97 % ee ) utilizing the alkylation of a malleable oxindole substrate. The utility of the methodology was demonstrated through a concise and highly enantioselective synthesis of (−)‐debromoflustramine B.