Asymmetric synthesis of isoindolones by chiral cyclopentadienyl-rhodium(III)-catalyzed C-H functionalizations.Angew Chem Int Ed Engl. 2014 Jul 21; 53(30):7896-9.AC
Abstract
Directed Cp*Rh(III)-catalyzed carbon-hydrogen (C-H) bond functionalizations have evolved as a powerful strategy for the construction of heterocycles. Despite their high value, the development of related asymmetric reactions is largely lagging behind due to a limited availability of robust and tunable chiral cyclopentadienyl ligands. Rhodium complexes comprising a chiral Cp ligand with an atropchiral biaryl backbone enables an asymmetric synthesis of isoindolones from arylhydroxamates and weakly alkyl donor/acceptor diazo derivatives as one-carbon component under mild conditions. The complex guides the substrates with a high double facial selectivity yielding the chiral isoindolones in good yields and excellent enantioselectivities.
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
24916401
Citation
Ye, Baihua, and Nicolai Cramer. "Asymmetric Synthesis of Isoindolones By Chiral cyclopentadienyl-rhodium(III)-catalyzed C-H Functionalizations." Angewandte Chemie (International Ed. in English), vol. 53, no. 30, 2014, pp. 7896-9.
Ye B, Cramer N. Asymmetric synthesis of isoindolones by chiral cyclopentadienyl-rhodium(III)-catalyzed C-H functionalizations. Angew Chem Int Ed Engl. 2014;53(30):7896-9.
Ye, B., & Cramer, N. (2014). Asymmetric synthesis of isoindolones by chiral cyclopentadienyl-rhodium(III)-catalyzed C-H functionalizations. Angewandte Chemie (International Ed. in English), 53(30), 7896-9. https://doi.org/10.1002/anie.201404895
Ye B, Cramer N. Asymmetric Synthesis of Isoindolones By Chiral cyclopentadienyl-rhodium(III)-catalyzed C-H Functionalizations. Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7896-9. PubMed PMID: 24916401.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Asymmetric synthesis of isoindolones by chiral cyclopentadienyl-rhodium(III)-catalyzed C-H functionalizations.
AU - Ye,Baihua,
AU - Cramer,Nicolai,
Y1 - 2014/06/10/
PY - 2014/05/02/received
PY - 2014/6/12/entrez
PY - 2014/6/12/pubmed
PY - 2014/6/12/medline
KW - CH activation
KW - asymmetric catalysis
KW - cyclopentadienyl ligand
KW - diazo ester
KW - rhodium
SP - 7896
EP - 9
JF - Angewandte Chemie (International ed. in English)
JO - Angew Chem Int Ed Engl
VL - 53
IS - 30
N2 - Directed Cp*Rh(III)-catalyzed carbon-hydrogen (C-H) bond functionalizations have evolved as a powerful strategy for the construction of heterocycles. Despite their high value, the development of related asymmetric reactions is largely lagging behind due to a limited availability of robust and tunable chiral cyclopentadienyl ligands. Rhodium complexes comprising a chiral Cp ligand with an atropchiral biaryl backbone enables an asymmetric synthesis of isoindolones from arylhydroxamates and weakly alkyl donor/acceptor diazo derivatives as one-carbon component under mild conditions. The complex guides the substrates with a high double facial selectivity yielding the chiral isoindolones in good yields and excellent enantioselectivities.
SN - 1521-3773
UR - https://www.unboundmedicine.com/medline/citation/24916401/Asymmetric_synthesis_of_isoindolones_by_chiral_cyclopentadienyl_rhodium_III__catalyzed_C_H_functionalizations_
DB - PRIME
DP - Unbound Medicine
ER -