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Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization.
Org Lett. 2014 Nov 21; 16(22):5910-3.OL

Abstract

Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures.

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Authors+Show Affiliations

Mantelingu K
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Lin Y
No affiliation info available
Seidel D
No affiliation info available

MeSH

AldehydesAminesAzo CompoundsBenzoic AcidCatalysisCyclizationCycloaddition ReactionHeterocyclic Compounds, 4 or More RingsMolecular StructureOxidation-ReductionStereoisomerismTetrahydroisoquinolinesThiosemicarbazones

Pub Type(s)

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

Language

eng

PubMed ID

25413125

Citation

Mantelingu, Kempegowda, et al. "Intramolecular [3 + 2]-cycloadditions of Azomethine Ylides Derived From Secondary Amines Via Redox-neutral C-H Functionalization." Organic Letters, vol. 16, no. 22, 2014, pp. 5910-3.
Mantelingu K, Lin Y, Seidel D. Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization. Org Lett. 2014;16(22):5910-3.
Mantelingu, K., Lin, Y., & Seidel, D. (2014). Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization. Organic Letters, 16(22), 5910-3. https://doi.org/10.1021/ol502918g
Mantelingu K, Lin Y, Seidel D. Intramolecular [3 + 2]-cycloadditions of Azomethine Ylides Derived From Secondary Amines Via Redox-neutral C-H Functionalization. Org Lett. 2014 Nov 21;16(22):5910-3. PubMed PMID: 25413125.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization. AU - Mantelingu,Kempegowda, AU - Lin,Yingfu, AU - Seidel,Daniel, Y1 - 2014/11/03/ PY - 2014/11/22/entrez PY - 2014/11/22/pubmed PY - 2015/8/4/medline SP - 5910 EP - 3 JF - Organic letters JO - Org Lett VL - 16 IS - 22 N2 - Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25413125/Intramolecular_[3_+_2]_cycloadditions_of_azomethine_ylides_derived_from_secondary_amines_via_redox_neutral_C_H_functionalization_ DB - PRIME DP - Unbound Medicine ER -