Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates.Org Lett. 2008 Jun 19; 10(12):2425-8.OL
Abstract
The allylic amination of acetates and carbonates affords dehydro-beta-aminoesters, which are useful precursors of biologically active compounds. The uncatalyzed reaction proceeds via a S(N)2' mechanism. On the other hand, under palladium-catalyzed conditions, the reaction shows a strong solvent-dependent regiocontrol, affording exclusively one of the two possible regioisomers with complete transfer of chirality from the substrates to the products.
Links
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
18484731
Citation
Benfatti, Fides, et al. "Synthesis of Dehydro-beta-amino Esters Via Highly Regioselective Amination of Allylic Carbonates." Organic Letters, vol. 10, no. 12, 2008, pp. 2425-8.
Benfatti F, Cardillo G, Gentilucci L, et al. Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates. Org Lett. 2008;10(12):2425-8.
Benfatti, F., Cardillo, G., Gentilucci, L., Mosconi, E., & Tolomelli, A. (2008). Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates. Organic Letters, 10(12), 2425-8. https://doi.org/10.1021/ol8006919
Benfatti F, et al. Synthesis of Dehydro-beta-amino Esters Via Highly Regioselective Amination of Allylic Carbonates. Org Lett. 2008 Jun 19;10(12):2425-8. PubMed PMID: 18484731.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates.
AU - Benfatti,Fides,
AU - Cardillo,Giuliana,
AU - Gentilucci,Luca,
AU - Mosconi,Elisa,
AU - Tolomelli,Alessandra,
Y1 - 2008/05/17/
PY - 2008/5/20/pubmed
PY - 2008/8/8/medline
PY - 2008/5/20/entrez
SP - 2425
EP - 8
JF - Organic letters
JO - Org Lett
VL - 10
IS - 12
N2 - The allylic amination of acetates and carbonates affords dehydro-beta-aminoesters, which are useful precursors of biologically active compounds. The uncatalyzed reaction proceeds via a S(N)2' mechanism. On the other hand, under palladium-catalyzed conditions, the reaction shows a strong solvent-dependent regiocontrol, affording exclusively one of the two possible regioisomers with complete transfer of chirality from the substrates to the products.
SN - 1523-7060
UR - https://www.unboundmedicine.com/medline/citation/18484731/Synthesis_of_dehydro_beta_amino_esters_via_highly_regioselective_amination_of_allylic_carbonates_
L2 - https://doi.org/10.1021/ol8006919
DB - PRIME
DP - Unbound Medicine
ER -
