4.5 Article

Asymmetric Sequential Aza-Diels-Alder and O-Michael Addition: Efficient Construction of Chiral Hydropyrano[2,3-b]pyridines

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 30, Issue 11, Pages 2669-2675

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201200942

Keywords

asymmetric organocatalysis; aza-Diels-Alder; O-Michael addition; hemiaminal; pyrano[2,3-b]-pyridines

Funding

  1. Natural Science Foundation of China [20972101, 21125206]

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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 alpha,beta-unsaturated ketone motif. A tandem O-Michael addition reaction was completed via acid catalysis.

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