Asymmetric synthesis of enantioenriched α-allyl esters through Pd(BINAPHANE)-catalysed allylation of disubstituted ketenes

被引：1
|
作者：
Ibrahim, Ahmad A.
O'Reilly, Stephen C. J.
Bottarel, Margot
Kerrigan, Nessan J.
机构：
[1] School of Chemical Sciences and Life Sciences Institute, Dublin City University, Glasnevin
[2] Department of Chemistry, Oakland University, 2200 N. Squirrel Rd, Rochester, 48309, MI
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 24期
关键词：
BETA-LACTONES; CATALYZED REACTIONS; ALKYLATION; CARBONATES; ACETATES; AMINES;
D O I：
10.1039/d4cc00057a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Pd2dba3 center dot CHCl3 (2.5 mol%)-BINAPHANE (5 mol%) was used to promote the first catalytic enantioselective allylation of disubstituted ketenes to give alpha-allyl esters. The ester products were formed in good to excellent yields (61-93% yield for 13 examples, 16 examples in all), with moderate to good enantioselectivity (68-80% ee for 7 examples). A Pd2dba3 center dot CHCl3 (2.5 mol%)-BINAPHANE (5 mol%) catalytic system promotes the enantioselective allylation of disubstituted ketenes to give alpha-allyl esters.
引用
收藏
页码：3283 / 3286
页数：4
相关论文
共 50 条
  • [1] Asymmetric double allylation of 1,4-dicarbonyl compounds with enantioenriched allyl bis(boronate) esters
    Ferris, Grace E.
    Hong, Kai
    Roundtree, Ian A.
    Morken, James P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [2] BINAPHANE-Catalyzed Asymmetric Synthesis of trans-β-Lactams from Disubstituted Ketenes and N-Tosyl Arylimines
    Chen, Shi
    Salo, Eric C.
    Wheeler, Kraig A.
    Kerrigan, Nessan J.
    ORGANIC LETTERS, 2012, 14 (07) : 1784 - 1787
  • [3] Proline-catalysed asymmetric amination of α,α-disubstituted aldehydes:: synthesis of configurationally stable enantioenriched α-aminoaldehydes
    Vogt, H
    Vanderheiden, S
    Bräse, S
    CHEMICAL COMMUNICATIONS, 2003, (19) : 2448 - 2449
  • [4] Synthesis of Enantioenriched α,α-Difluoro-β-arylbutanoic Esters by Pd-Catalyzed Asymmetric Hydrogenation
    Feng, Sitian
    Tang, Yitian
    Yang, Chenjue
    Shen, Chaoren
    Dong, Kaiwu
    ORGANIC LETTERS, 2020, 22 (19) : 7508 - 7512
  • [5] Catalytic asymmetric synthesis of esters from ketenes
    Wiskur, SL
    Fu, GC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) : 6176 - 6177
  • [6] A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters
    Albat, Dominik
    Neudoerfl, Joerg-Martin
    Schmalz, Hans-Guenther
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (14) : 2099 - 2102
  • [7] Enantioenriched allyl bis(boronate) esters: Versatile reagents in organic synthesis
    Ferris, Grace E.
    Kliman, Laura T.
    Mlynarski, Scott N.
    Hong, Kai
    Roundtree, Ian A.
    Chang, Weng K.
    Morken, James P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [8] Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral π-allyl Pd-catalyst
    Kitagawa, O
    Yotsumoto, K
    Kohriyama, M
    Dobashi, Y
    Taguchi, T
    ORGANIC LETTERS, 2004, 6 (20) : 3605 - 3607
  • [9] Enantioselective synthesis of γ-butenolides through Pd-catalysed C5-selective allylation of siloxyfurans
    Richard, Francois
    Aubert, Sidonie
    Katsina, Tania
    Reinalda, Luuk
    Palomas, David
    Crespo-Otero, Rachel
    Huang, Jingjun
    Leitch, David C.
    Mateos, Carlos
    Arseniyadis, Stellios
    NATURE SYNTHESIS, 2022, 1 (08): : 641 - 648
  • [10] Enantioselective synthesis of γ-butenolides through Pd-catalysed C5-selective allylation of siloxyfurans
    François Richard
    Sidonie Aubert
    Tania Katsina
    Luuk Reinalda
    David Palomas
    Rachel Crespo-Otero
    Jingjun Huang
    David C. Leitch
    Carlos Mateos
    Stellios Arseniyadis
    Nature Synthesis, 2022, 1 : 641 - 648
12345