Tertiary Amine Mediated Tandem Cross‐Rauhut–Currier/Acetalization Reactions: Access to Functionalized Spiro‐3,4‐Dihydropyrans | Zendy

Yao Weijun | Zendy; Wu Yihua | Zendy; Wang Gang | Zendy; Zhang Yiping | Zendy; Ma Cheng | Zendy

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Tertiary Amine Mediated Tandem Cross‐Rauhut–Currier/Acetalization Reactions: Access to Functionalized Spiro‐3,4‐Dihydropyrans

Author(s) -

Yao Weijun,

Wu Yihua,

Wang Gang,

Zhang Yiping,

Ma Cheng

Publication year - 2009

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200905091

Subject(s) - chemistry , halide , tandem , amine gas treating , quaternary carbon , medicinal chemistry , catalysis , organic chemistry , polymer chemistry , materials science , enantioselective synthesis , composite material

γ‐Proton transfer furnished the highly selective title reaction in which cyclic β‐haloenals 1 react with β,γ‐unsaturated α‐ketoesters 2 to generate functionalized spiro‐3,4‐dihydro‐2 H ‐pyrans 3 having an α‐quaternary carbon center and an adjacent vinyl halide group in skeleton. DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene, Tos=4‐toluenesulfonyl.

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