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Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance.
Org Lett. 2014 Aug 01; 16(15):4036-9.OL

Abstract

Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.

Authors+Show Affiliations

Department of Chemistry, Iowa State University , 1605 Gilman Hall, Ames, Iowa 50014, United States.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

25020184

Citation

Du, Xiang-Wei, et al. "Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles By Rh-catalyzed Alkene Hydroacylation: Constructing Six-membered Rings in the Absence of Chelation Assistance." Organic Letters, vol. 16, no. 15, 2014, pp. 4036-9.
Du XW, Ghosh A, Stanley LM. Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance. Org Lett. 2014;16(15):4036-9.
Du, X. W., Ghosh, A., & Stanley, L. M. (2014). Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance. Organic Letters, 16(15), 4036-9. https://doi.org/10.1021/ol501869s
Du XW, Ghosh A, Stanley LM. Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles By Rh-catalyzed Alkene Hydroacylation: Constructing Six-membered Rings in the Absence of Chelation Assistance. Org Lett. 2014 Aug 1;16(15):4036-9. PubMed PMID: 25020184.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance. AU - Du,Xiang-Wei, AU - Ghosh,Avipsa, AU - Stanley,Levi M, Y1 - 2014/07/14/ PY - 2014/7/15/entrez PY - 2014/7/16/pubmed PY - 2014/10/11/medline SP - 4036 EP - 9 JF - Organic letters JO - Org. Lett. VL - 16 IS - 15 N2 - Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25020184/Enantioselective_synthesis_of_polycyclic_nitrogen_heterocycles_by_Rh_catalyzed_alkene_hydroacylation:_constructing_six_membered_rings_in_the_absence_of_chelation_assistance_ L2 - https://dx.doi.org/10.1021/ol501869s DB - PRIME DP - Unbound Medicine ER -