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Formal enantioselective total synthesis of schulzeines A-C via Pd-catalyzed intramolecular asymmetric allylic amination.
J Org Chem. 2011 Aug 05; 76(15):6240-9.JO

Abstract

Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Lin CF
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA.
Ojima I
No affiliation info available

MeSH

Allyl CompoundsAminationCatalysisHeterocyclic Compounds, 3-RingLactamsLigandsMolecular StructurePalladiumQuinolizidinesStereoisomerismSulfuric Acid Esters

Pub Type(s)

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

Language

eng

PubMed ID

21671593

Citation

Lin, Chi-Feng, and Iwao Ojima. "Formal Enantioselective Total Synthesis of Schulzeines A-C Via Pd-catalyzed Intramolecular Asymmetric Allylic Amination." The Journal of Organic Chemistry, vol. 76, no. 15, 2011, pp. 6240-9.
Lin CF, Ojima I. Formal enantioselective total synthesis of schulzeines A-C via Pd-catalyzed intramolecular asymmetric allylic amination. J Org Chem. 2011;76(15):6240-9.
Lin, C. F., & Ojima, I. (2011). Formal enantioselective total synthesis of schulzeines A-C via Pd-catalyzed intramolecular asymmetric allylic amination. The Journal of Organic Chemistry, 76(15), 6240-9. https://doi.org/10.1021/jo2009615
Lin CF, Ojima I. Formal Enantioselective Total Synthesis of Schulzeines A-C Via Pd-catalyzed Intramolecular Asymmetric Allylic Amination. J Org Chem. 2011 Aug 5;76(15):6240-9. PubMed PMID: 21671593.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Formal enantioselective total synthesis of schulzeines A-C via Pd-catalyzed intramolecular asymmetric allylic amination. AU - Lin,Chi-Feng, AU - Ojima,Iwao, Y1 - 2011/07/08/ PY - 2011/6/16/entrez PY - 2011/6/16/pubmed PY - 2012/1/18/medline SP - 6240 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 15 N2 - Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21671593/Formal_enantioselective_total_synthesis_of_schulzeines_A_C_via_Pd_catalyzed_intramolecular_asymmetric_allylic_amination_ L2 - https://doi.org/10.1021/jo2009615 DB - PRIME DP - Unbound Medicine ER -