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Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O-H Insertion Reactions.
Chem Pharm Bull (Tokyo). 2018; 66(10):1006-1014.CP

Abstract

Centrally chiral bisoxazolines connected directly to a planar chiral [2.2]paracyclophane backbone were synthesized and evaluated as asymmetric ligands in Cu-catalyzed intermolecular ethanolic O-H insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2]paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular aromatic O-H insertion reactions, without the aid of central chirality.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kitagaki S
Faculty of Pharmacy, Meijo University.
Murata S
Faculty of Pharmacy, Meijo University.
Asaoka K
Faculty of Pharmacy, Meijo University.
Sugisaka K
Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University.
Mukai C
Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University.
Takenaga N
Faculty of Pharmacy, Meijo University.
Yoshida K
Faculty of Pharmacy, Meijo University.

MeSH

CatalysisCopperDrug DesignHydroxidesLigandsMolecular StructurePolycyclic CompoundsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30270235

Citation

Kitagaki, Shinji, et al. "Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O-H Insertion Reactions." Chemical & Pharmaceutical Bulletin, vol. 66, no. 10, 2018, pp. 1006-1014.
Kitagaki S, Murata S, Asaoka K, et al. Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O-H Insertion Reactions. Chem Pharm Bull (Tokyo). 2018;66(10):1006-1014.
Kitagaki, S., Murata, S., Asaoka, K., Sugisaka, K., Mukai, C., Takenaga, N., & Yoshida, K. (2018). Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O-H Insertion Reactions. Chemical & Pharmaceutical Bulletin, 66(10), 1006-1014. https://doi.org/10.1248/cpb.c18-00519
Kitagaki S, et al. Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O-H Insertion Reactions. Chem Pharm Bull (Tokyo). 2018;66(10):1006-1014. PubMed PMID: 30270235.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O-H Insertion Reactions. AU - Kitagaki,Shinji, AU - Murata,Shunsuke, AU - Asaoka,Kisaki, AU - Sugisaka,Kenta, AU - Mukai,Chisato, AU - Takenaga,Naoko, AU - Yoshida,Keisuke, PY - 2018/10/2/entrez PY - 2018/10/3/pubmed PY - 2018/10/16/medline KW - O–H insertion KW - bisoxazoline KW - copper KW - cyclophane KW - planar chirality SP - 1006 EP - 1014 JF - Chemical & pharmaceutical bulletin JO - Chem Pharm Bull (Tokyo) VL - 66 IS - 10 N2 - Centrally chiral bisoxazolines connected directly to a planar chiral [2.2]paracyclophane backbone were synthesized and evaluated as asymmetric ligands in Cu-catalyzed intermolecular ethanolic O-H insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2]paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular aromatic O-H insertion reactions, without the aid of central chirality. SN - 1347-5223 UR - https://www.unboundmedicine.com/medline/citation/30270235/Planar_Chiral_[2_2]Paracyclophane_Based_Bisoxazoline_Ligands:_Design_Synthesis_and_Use_in_Cu_Catalyzed_Inter__and_Intramolecular_Asymmetric_O_H_Insertion_Reactions_ DB - PRIME DP - Unbound Medicine ER -