Reverse regioselectivity in Pd(0)/InI-mediated allylation of aldehydes with ε-amido-allylindiums generated from β-lactams. A new entry to non-racemic highly substituted γ-butyrolactones

ε-Amido-allylindiums generated from N -Ts-β-lactams in the presence of 2 eq. of InI, catalytic amounts of Pd(PPh 3 ) 4 and 5 eq. of CF 3 CO 2 H react regio- and stereoselectively with a number of aromatic and aliphatic aldehydes to afford γ-butyrolactones as the exclusive products in high yield.

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Bibliographic Details
Published in:RSC advances 2016-01, Vol.6 (31), p.26451-26460
Main Authors: Klimczak, Urszula, Staszewska-Krajewska, Olga, Zambroń, Bartosz K.
Format: Article
Language:English
Subjects:
Aldehydes
Aliphatic compounds
Allyl compounds
Catalysis
Catalysts
Chemical reactions
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Description
Summary:ε-Amido-allylindiums generated from N -Ts-β-lactams in the presence of 2 eq. of InI, catalytic amounts of Pd(PPh 3 ) 4 and 5 eq. of CF 3 CO 2 H react regio- and stereoselectively with a number of aromatic and aliphatic aldehydes to afford γ-butyrolactones as the exclusive products in high yield.
ISSN:2046-2069
2046-2069
DOI:10.1039/C6RA00517A