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Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β‐Keto Esters
Author(s) -
Shibatomi Kazutaka,
Kotozaki Manato,
Sasaki Nozomi,
Fujisawa Ikuhide,
Iwasa Seiji
Publication year - 2015
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.201502042
Subject(s) - enantioselective synthesis , stereocenter , phenols , chemistry , ether , organic chemistry , lewis acids and bases , carbon fibers , catalysis , stereochemistry , materials science , composite number , composite material
Abstract The enantioselective formation of α‐aryloxy‐β‐keto esters is described for the first time. Lewis acid catalyzed enantioselective chlorination of β‐keto esters and subsequent S N 2 reactions with phenols yielded α‐aryloxy‐β‐keto esters with up to 96 % ee . Favorskii rearrangement of α‐chloro‐β‐keto esters was also found to give 1,2‐diesters with slightly reduced enantiopurity.