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Asymmetric Lewis Acid Catalyzed Addition of Isocyanides to Aldehydes – Synthesis of 5‐Amino‐2‐(1‐hydroxyalkyl)oxazoles
Author(s) -
Wang Shixin,
Wang MeiXiang,
Wang DeXian,
Zhu Jieping
Publication year - 2007
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.200700340
Subject(s) - chemistry , oxazole , acetaldehyde , catalysis , enantiomer , lewis acids and bases , enantiomeric excess , chloride , medicinal chemistry , organic chemistry , enantioselective synthesis , ethanol
Stannous chloride efficiently catalyzes condensations between α‐isocyanoacetamides ( 1 ) and a variety of aldehydes to afford the corresponding 5‐amino‐2‐(1‐hydroxyalkyl)oxazoles ( 3 ) in good to excellent yields. The [Sn‐( R )‐Ph‐PyBox](OTf) 2 ‐catalyzed reaction between 1a and 2‐(benzyloxy)acetaldehyde ( 2g ) shows an isoinversion effect, with the maximum enantiomeric excess of oxazole 3g (80 %) being obtained at –40 °C. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)