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Pd-catalyzed asymmetric allylic etherification using chiral biphenol-based diphosphinite ligands and its application for the formal total synthesis of (-)-galanthamine.
J Org Chem. 2013 Apr 19; 78(8):4013-8.JO

Abstract

A library of novel chiral biphenol-based diphosphinite (BOP) ligands was designed and created. These BOP ligands were applied to a Pd-catalyzed intermolecular allylic etherification reaction, which provided a key intermediate for the formal total synthesis of (-)-galanthamine with 97% ee in 97% yield.

Authors+Show Affiliations

Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, USA.No affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23472673

Citation

Zang, Yang, and Iwao Ojima. "Pd-catalyzed Asymmetric Allylic Etherification Using Chiral Biphenol-based Diphosphinite Ligands and Its Application for the Formal Total Synthesis of (-)-galanthamine." The Journal of Organic Chemistry, vol. 78, no. 8, 2013, pp. 4013-8.
Zang Y, Ojima I. Pd-catalyzed asymmetric allylic etherification using chiral biphenol-based diphosphinite ligands and its application for the formal total synthesis of (-)-galanthamine. J Org Chem. 2013;78(8):4013-8.
Zang, Y., & Ojima, I. (2013). Pd-catalyzed asymmetric allylic etherification using chiral biphenol-based diphosphinite ligands and its application for the formal total synthesis of (-)-galanthamine. The Journal of Organic Chemistry, 78(8), 4013-8. https://doi.org/10.1021/jo400355j
Zang Y, Ojima I. Pd-catalyzed Asymmetric Allylic Etherification Using Chiral Biphenol-based Diphosphinite Ligands and Its Application for the Formal Total Synthesis of (-)-galanthamine. J Org Chem. 2013 Apr 19;78(8):4013-8. PubMed PMID: 23472673.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd-catalyzed asymmetric allylic etherification using chiral biphenol-based diphosphinite ligands and its application for the formal total synthesis of (-)-galanthamine. AU - Zang,Yang, AU - Ojima,Iwao, Y1 - 2013/03/29/ PY - 2013/3/12/entrez PY - 2013/3/12/pubmed PY - 2013/8/13/medline SP - 4013 EP - 8 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 8 N2 - A library of novel chiral biphenol-based diphosphinite (BOP) ligands was designed and created. These BOP ligands were applied to a Pd-catalyzed intermolecular allylic etherification reaction, which provided a key intermediate for the formal total synthesis of (-)-galanthamine with 97% ee in 97% yield. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23472673/Pd_catalyzed_asymmetric_allylic_etherification_using_chiral_biphenol_based_diphosphinite_ligands_and_its_application_for_the_formal_total_synthesis_of_____galanthamine_ L2 - https://doi.org/10.1021/jo400355j DB - PRIME DP - Unbound Medicine ER -