Enantioselective Alkylation of 2‐Oxindoles Catalyzed by a Bifunctional Phase‐Transfer Catalyst: Synthesis of (−)‐Debromoflustramine B | Zendy

Craig Ryan | Zendy; Sorrentino Emiliano | Zendy; Con Stephen J. | Zendy

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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.

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