Enantioselective synthesis of acyclic allylic esters catalyzed by a palladium/BINAP(S) system

[Display omitted] The synthesis of chiral nonracemic acyclic allylic pivalates via the Pd-catalyzed allylic substitution of racemic allylic carbonates is presented. Good to excellent enantioselectivities (up to 90%) were observed in several cases. An extraordinarily high preference for the productio...

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Bibliographic Details
Published in:Tetrahedron letters 2004-10, Vol.45 (41), p.7613-7616
Main Authors: Faller, J.W., Wilt, Jeremy C.
Format: Article
Language:English
Subjects:
Asymmetric allylation
Catalysis
Palladium
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Summary:[Display omitted] The synthesis of chiral nonracemic acyclic allylic pivalates via the Pd-catalyzed allylic substitution of racemic allylic carbonates is presented. Good to excellent enantioselectivities (up to 90%) were observed in several cases. An extraordinarily high preference for the production of the branched regioisomeric product is seen when starting from 3-buten-2-yl and crotyl substrates. A significant kinetic resolution ( k rel = 38) of the 1,3-dimethylallyl substrate was also observed, leading to the production of esters of both enantiomers of an allylic alcohol with a single enantiomer of catalyst.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.08.105