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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.