Fe(OTf)3-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure

被引:0
|
作者
Lu Min [1 ,2 ]
Yang Aimei [1 ]
Zhang Yu [1 ,2 ]
Sun Jianting [2 ]
Wei Bangguo [2 ]
机构
[1] Lanzhou Univ Technol, Sch Life Sci & Engn, Lanzhou 730050, Peoples R China
[2] Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
iminonium; N; O-acetal; boronic ester; addition reaction; CROSS-COUPLING REACTION; REGIOSELECTIVE GLYCOSYLATION; ASYMMETRIC-SYNTHESIS; IXAZOMIB CITRATE; TRANSESTERIFICATION; DERIVATIVES; CHEMISTRY; ACIDS;
D O I
10.6023/cjoc202301017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient approach acess to boronic ester containing N,O-acetal structure has been established through the Fe(OTf)(3)-catalyzed addition of N,O-acetal with organic boric acid. A series of N-O-acetal boronic ester compounds have been successfully prepared in 58%similar to 98% yields. Moreover, these compounds retain the property of boronic ester and can be used for coupling reaction.
引用
收藏
页码:1777 / 1785
页数:9
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共 64 条
  • [31] Transition Metal Catalyzed Asymmetric Hydroboration of Internal Alkenes
    Lu Houxiang
    Li Bijie
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3167 - 3182
  • [32] Bortezomib, melphalan, and prednisone versus bortezomib, thalidomide, and prednisone as induction therapy followed by maintenance treatment with bortezomib and thalidomide versus bortezomib and prednisone in elderly patients with untreated multiple myeloma: a randomised trial
    Mateos, Maria-Victoria
    Oriol, Albert
    Martinez-Lopez, Joaquin
    Gutierrez, Norma
    Teruel, Ana-Isabel
    de Paz, Raquel
    Garcia-Larana, Jose
    Bengoechea, Enrique
    Martin, Alejandro
    Diaz Mediavilla, Joaquin
    Palomera, Luis
    de Arriba, Felipe
    Gonzalez, Yolanda
    Hernandez, Jose-Mariano
    Sureda, Ana
    Bello, Jose-Luis
    Bargay, Joan
    Penalver, Francisco-Javier
    Ribera, Jose-Maria
    Martin-Mateos, Maria-Luisa
    Garcia-Sanz, Ramon
    Cibeira, Maria-Teresa
    Martin Ramos, Maria-Luisa
    Vidriales, Maria-Belen
    Paiva, Bruno
    Montalban, Maria-Angeles
    Lahuerta, Juan-Jose
    Blade, Joan
    San Miguel, Jesus-Fernando
    [J]. LANCET ONCOLOGY, 2010, 11 (10) : 934 - 941
  • [33] Boronic Esters in Asymmetric Synthesis
    Matteson, Donald S.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) : 10009 - 10023
  • [34] Applications of organoboron compounds in carbohydrate chemistry and glycobiology: analysis, separation, protection, and activation
    McClary, Corey A.
    Taylor, Mark S.
    [J]. CARBOHYDRATE RESEARCH, 2013, 381 : 112 - 122
  • [35] Mei S. J., 2021, CHINESE J ORG CHEM, V41, P2914
  • [36] Seven-membered ring boronates at trans-diol moieties of carbohydrates
    Meiland, Marcel
    Heinze, Thomas
    Guenther, Wolfgang
    Liebert, Tim
    [J]. TETRAHEDRON LETTERS, 2009, 50 (04) : 469 - 472
  • [37] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
    MIYAURA, N
    SUZUKI, A
    [J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483
  • [38] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES
    MIYAURA, N
    YANAGI, T
    SUZUKI, A
    [J]. SYNTHETIC COMMUNICATIONS, 1981, 11 (07) : 513 - 519
  • [39] Regioselective and 1,2-cis--Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst
    Nakagawa, Akira
    Tanaka, Masamichi
    Hanamura, Shun
    Takahashi, Daisuke
    Toshima, Kazunobu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (37) : 10935 - 10939
  • [40] REGIOSELECTIVE GLYCOSYLATION OF UNPROTECTED METHYL HEXOPYRANOSIDE BY TRANSIENT MASKING WITH ARYLBORONIC ACID
    Nishino, Takashi
    Ohya, Yohei
    Murai, Rie
    Shirahata, Tatsuya
    Yamamoto, Daisuke
    Makino, Kazuishi
    Kaji, Eisuke
    [J]. HETEROCYCLES, 2012, 84 (02) : 1123 - 1140