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Asymmetric Synthesis of 5‐(1‐Hydroxyalkyl)tetrazoles by Catalytic Enantioselective Passerini‐Type Reactions
Author(s) -
Yue Tao,
Wang MeiXiang,
Wang DeXian,
Zhu Jieping
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200804213
Subject(s) - enantioselective synthesis , catalysis , acrolein , chemistry , hydrazoic acid , enantiomeric excess , toluene , substrate (aquarium) , enantiomer , organic chemistry , combinatorial chemistry , oceanography , geology
Three‐part harmony : Three‐component Passerini reactions (P‐3CR, see Scheme) of a wide range of aldehydes 2 and isocyanides 3 , with hydrazoic acid 4 in toluene, in the presence of a [(salen)AlMe]‐complex catalyst afford 5‐(1‐hydroxyalkyl)tetrazoles 1 in good‐to‐excellent yields and enantiomeric excess. A tandem Michael addition/enantioselective P‐3CR, using an acrolein substrate, affords highly functionalized tetrazoles.