Asymmetric Lewis Acid Catalyzed Addition of Isocyanides to Aldehydes – Synthesis of 5‐Amino‐2‐(1‐hydroxyalkyl)oxazoles | Zendy

Wang Shixin | Zendy; Wang MeiXiang | Zendy; Wang DeXian | Zendy; Zhu Jieping | Zendy

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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)

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