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Asymmetric Sequential Aza‐Diels‐Alder and O ‐Michael Addition: Efficient Construction of Chiral Hydropyrano[2,3 ‐b ]pyridines
Author(s) -
Yin Xiang,
Zhou Qingqing,
Dong Lin,
Chen Yingchun
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200942
Subject(s) - chemistry , michael reaction , stereoselectivity , tandem , ketone , methyl vinyl ketone , pyridine , adduct , stereochemistry , catalysis , diels–alder reaction , organic chemistry , materials science , composite material
Abstract An asymmetric aza‐Diels‐Alder and O ‐Michael addition sequence has been developed to construct chiral hydropyrano[2,3 ‐b ]pyridine derivatives with good yields and excellent stereoselectivity, by starting with N ‐Ts‐1‐aza‐1,3‐butadienes and aliphatic aldehydes tethered to an α , β ‐unsaturated ketone motif. A tandem O ‐Michael addition reaction was completed via acid catalysis.