A Lewis Acid-Catalyzed Diastereoselective Synthesis of Functionalized 2-Diazo-1,5-dicarbonyl Compounds

被引：10
|
作者：
Howard, Evan M. [1 ]
Brewer, Matthias [1 ]
机构：
[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA
来源：
ACS CATALYSIS | 2021年 / 11卷 / 19期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
conjugate addition; vinyl diazonium; diastereoselective; vinyl cation; 1,4-addition; Mukaiyama-Michael; furan; cation; FRAGMENTATION; ALKENEDIAZONIUM; CRYSTAL; ACETALS; KETONES; SALTS;
D O I：
10.1021/acscatal.1c03036
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A diverse array of 2-diazo-1,5-dicarbonyl compounds were formed by the Lewis acid-catalyzed reaction of enoxysilanes with beta-hydroxy-alpha-diazo carbonyls. This reaction proceeds via the Zn(OTf)(2)-catalyzed dehydroxylation of the beta-hydroxy-alpha-diazo carbonyl to form a vinyl diazonium ion intermediate that is intercepted by the enoxysilane nucleophile to give diazo-containing scaffolds with increased molecular complexity. The reaction appears to be general, and a variety of functional groups, including common protecting groups, are well tolerated. The 2-diazo-1,5-dicarbonyl products are formed in yields of up to 99% with diastereoselectivity up to >20:1.
引用
收藏
页码：12203 / 12207
页数：5
相关论文
共 50 条
  • [41] Lewis acid-catalyzed reductive etherification of carbonyl compounds with alkoxyhydrosilanes
    Miura, K
    Ootsuka, K
    Suda, S
    Nishikori, H
    Hosomi, A
    SYNLETT, 2002, (02) : 313 - 315
  • [42] CHEMISTRY OF ENOL ETHERS .73. SYNTHESIS OF PIRILIUM SALTS BASED ON MONOACETALS OF 1,5-DICARBONYL COMPOUNDS
    MAKIN, SM
    MARKINA, TA
    BOIKO, II
    ZHURNAL ORGANICHESKOI KHIMII, 1986, 22 (02): : 295 - 298
  • [43] SYNTHESIS AND PROPERTIES OF 2-DIAZO-1,3-DICARBONYL COMPOUNDS .5. SYNTHESIS AND 1,2-NUCLEOPHILIC REARRANGEMENTS OF SOME 2-DIAZO-3-OXY-1-CYCLOHEXANONES
    NIKOLAEV, VA
    ZHDANOVA, OV
    KOROBITSYNA, IK
    ZHURNAL ORGANICHESKOI KHIMII, 1982, 18 (03): : 559 - 572
  • [44] Acid-Catalyzed Synthesis of -Trifluoromethylthiolated Carbonyl Compounds
    Alazet, Sebastien
    Ismalaj, Ermal
    Glenadel, Quentin
    Le Bars, Didier
    Billard, Thierry
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (21) : 4607 - 4610
  • [45] Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dinner and 1,3-Dicarbonyl Compounds
    Huang, Wenbo
    Xu, Jing
    Liu, Changhui
    Chen, Zhiyan
    Gu, Yanlong
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05): : 2941 - 2950
  • [46] TRIFLUOROMETHANESULFONIC ACID-CATALYZED INTERACTION OF DIAZO-COMPOUNDS AND DIALKYLPHOSPHITES WITH PHOSPHONATES FORMATION
    POLOZOV, AM
    MUSTAFIN, AK
    ZHURNAL OBSHCHEI KHIMII, 1992, 62 (06): : 1429 - 1430
  • [47] Lewis Acid-Catalyzed Yne-Carbonyl Metathesis of Ynamides and Cyclobutanones: Facile Synthesis of Functionalized Alkylidenecyclobutanes
    Sun, Yu-Li
    Chen, Ling
    Cao, Jian
    Sun, Feng-Na
    Xu, Zheng
    Zheng, Zhan-Jiang
    Cui, Yu-Ming
    Xu, Li-Wen
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (02) : 374 - 377
  • [48] Diastereoselective Lewis acid mediated reductions of α-alkyl-β-functionalized carbonyl compounds
    Bartoli, G
    Bartolacci, M
    Giuliani, A
    Marcantoni, E
    Massaccesi, M
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (14) : 2867 - 2879
  • [49] Iron Lewis acid catalyzed reactions of aromatic aldehydes with diazo compounds.
    Mahmood, SJ
    Hossain, MI
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U491 - U491
  • [50] Lewis acid-catalyzed divergent synthesis of polysubstituted furans and pyrroles
    Li, Chenguang
    Cao, Tongxiang
    Zhu, Shifa
    ORGANIC CHEMISTRY FRONTIERS, 2025,
12345