Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols To Form γ-Lactams via Rhodium(III)-Catalyzed C-H Activation.Org Lett. 2016 11 04; 18(21):5668-5671.OL
Abstract
A mild, regiocontrolled coupling of aromatic and vinylic amides with α-allenols to form γ-lactams via rhodium(III)-catalyzed C-H activation has been demonstrated. This [4 + 1] annulation reaction provides an efficient method for the synthesis of isoindolinones and 1,5-dihydro-pyrrol-2-ones bearing a tetrasubstituted carbon atom α to the nitrogen atom with good functional group tolerance. The hydroxyl group in the allene substrate is essential in controlling the chemo- and regioselectivity of the reaction probably by coordination interaction with the rhodium catalyst.
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
27775366
Citation
Zhou, Zhi, et al. "Regiocontrolled Coupling of Aromatic and Vinylic Amides With α-Allenols to Form γ-Lactams Via Rhodium(III)-Catalyzed C-H Activation." Organic Letters, vol. 18, no. 21, 2016, pp. 5668-5671.
Zhou Z, Liu G, Lu X. Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols To Form γ-Lactams via Rhodium(III)-Catalyzed C-H Activation. Org Lett. 2016;18(21):5668-5671.
Zhou, Z., Liu, G., & Lu, X. (2016). Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols To Form γ-Lactams via Rhodium(III)-Catalyzed C-H Activation. Organic Letters, 18(21), 5668-5671.
Zhou Z, Liu G, Lu X. Regiocontrolled Coupling of Aromatic and Vinylic Amides With α-Allenols to Form γ-Lactams Via Rhodium(III)-Catalyzed C-H Activation. Org Lett. 2016 11 4;18(21):5668-5671. PubMed PMID: 27775366.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols To Form γ-Lactams via Rhodium(III)-Catalyzed C-H Activation.
AU - Zhou,Zhi,
AU - Liu,Guixia,
AU - Lu,Xiyan,
Y1 - 2016/10/24/
PY - 2016/11/5/pubmed
PY - 2016/11/5/medline
PY - 2016/11/5/entrez
SP - 5668
EP - 5671
JF - Organic letters
JO - Org Lett
VL - 18
IS - 21
N2 - A mild, regiocontrolled coupling of aromatic and vinylic amides with α-allenols to form γ-lactams via rhodium(III)-catalyzed C-H activation has been demonstrated. This [4 + 1] annulation reaction provides an efficient method for the synthesis of isoindolinones and 1,5-dihydro-pyrrol-2-ones bearing a tetrasubstituted carbon atom α to the nitrogen atom with good functional group tolerance. The hydroxyl group in the allene substrate is essential in controlling the chemo- and regioselectivity of the reaction probably by coordination interaction with the rhodium catalyst.
SN - 1523-7052
UR - https://www.unboundmedicine.com/medline/citation/27775366/Regiocontrolled_Coupling_of_Aromatic_and_Vinylic_Amides_with_α_Allenols_To_Form_γ_Lactams_via_Rhodium_III__Catalyzed_C_H_Activation_
DB - PRIME
DP - Unbound Medicine
ER -
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