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Practical Synthesis of β‐Carbonyl Phenyltetrazolesulfones and Investigations of Their Reactivities in Organocatalysis
Author(s) -
Zweifel Theo,
Nielsen Martin,
Overgaard Jacob,
Jacobsen Christian Borch,
Jørgensen Karl Anker
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001426
Subject(s) - chemistry , organocatalysis , enantioselective synthesis , yield (engineering) , organic chemistry , alkyl , aryl , catalysis , materials science , metallurgy
A practical synthesis of β‐carbonyl phenyltetrazolesulfones, useful for a series of enantioselective reactions, is shown. Aryl, alkyl and ester carbonyl compounds all proved to be efficiently synthesised, leading to products in up to >99 % yield over two steps. During this procedure, no special attention to conditions or laborious purification by chromatography is needed. Furthermore, X‐ray crystallography, kinetic studies, as well as NMR and IR investigations provide insights into the reactivities of these compounds in organocatalysis.