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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.

Authors+Show Affiliations

Faculty of Pharmacy, Meijo University.Faculty of Pharmacy, Meijo University.Faculty of Pharmacy, Meijo University.Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University.Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University.Faculty of Pharmacy, Meijo University.Faculty of Pharmacy, Meijo University.

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 -