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Chiral Brønsted Acid‐Promoted Enantioselective Desymmetrization in an Intramolecular Schmidt Reaction of Symmetric Azido 1,3‐Hexanediones: Asymmetric Synthesis of Azaquaternary Pyrroloazepine Skeletons
Author(s) -
Yang Ming,
Zhao YuMing,
Zhang ShuYu,
Tu YongQiang,
Zhang FuMin
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100171
Subject(s) - desymmetrization , enantioselective synthesis , stereocenter , intramolecular force , chemistry , stereochemistry , brønsted–lowry acid–base theory , schmidt reaction , organic chemistry , catalysis
The enantioselective desymmetrization of 2‐substituted‐2‐azidopropyl 1,3‐hexanediones through an asymmetric intramolecular Schmidt reaction using a chiral Brønsted acid has been developed for the first time. Synthetically interesting pyrroloazepine skeletons with an azaquaternary stereogenic center with up to 59 % ee are accessed effectively (see scheme; R=H, alkyl, or aryl).
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