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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 ).