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

-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. -Ami...

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Published in:RSC advances 2016-03, Vol.6 (31), p.26451-2646
Main Authors: Klimczak, Urszula, Staszewska-Krajewska, Olga, Zambro, Bartosz K
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Summary:-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. -Amido-allylindiums generated from 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 with a number of aromatic and aliphatic aldehydes to afford trisubstituted γ -butyrolactones in high yield.
ISSN:2046-2069
DOI:10.1039/c6ra00517a