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Synthesis of β‐Lactams by 4‐ exo‐tet Cyclization Process Induced by Electrogenerated Cyanomethyl Anion, Part 2: [1] Stereochemical Implications
Author(s) -
Feroci Marta
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700156
Subject(s) - chemistry , hexafluorophosphate , deprotonation , acetonitrile , medicinal chemistry , amine gas treating , tetraethylammonium , methylene , chiral auxiliary , ion , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis , ionic liquid , potassium
An efficient electrochemically induced synthesis of chiral cis β‐lactams has been described, via deprotonation of chiral amides containing an acidic methylene group and a bromine atom as leaving group and bearing a chiral auxiliary or amine function. The electrogenerated base – cyanomethyl anion – is easily obtained by galvanostatic reduction of acetonitrile‐tetraethylammonium hexafluorophosphate solutions under very mild conditions. The yields are high and the cis ‐diastereoselection complete. The use of starting chiral amides has allowed in many cases the preparation of the most abundant isomer in a pure form.