Expeditious Assembly of a 2‐Amino‐4 H ‐chromene Skeleton by Using an Enantioselective Mannich Intramolecular Ring Cyclization–Tautomerization Cascade Sequence | Zendy

Ren Qiao | Zendy; Siau WoonYew | Zendy; Du Zhiyun | Zendy; Zhang Kun | Zendy; Wang Jian | Zendy

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Expeditious Assembly of a 2‐Amino‐4 H ‐chromene Skeleton by Using an Enantioselective Mannich Intramolecular Ring Cyclization–Tautomerization Cascade Sequence

Author(s) -

Ren Qiao,

Siau WoonYew,

Du Zhiyun,

Zhang Kun,

Wang Jian

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201100927

Subject(s) - enantioselective synthesis , tautomer , intramolecular force , ring (chemistry) , malononitrile , chemistry , enantiomer , stereochemistry , combinatorial chemistry , cascade , organic chemistry , catalysis , chromatography

Easy to assemble! An enantioselective cascade Mannich intramolecular ring cyclization–tautomerization reaction of malononitrile with 2‐hydroxyl N‐protected α‐amido sulfone is described (see scheme), which provides a new route to the synthesis of the privileged scaffold 2‐amino‐4 H ‐chromene in high yields (up to 94 %) and with good to high enantiomeric excesses (74–89 % ee ).

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