Asymmetric Auto-Tandem Catalysis with Chiral Organosuperbases: Intramolecular Cyclization/Enantioselective Direct Mannich-Type Addition Sequence

被引：0
作者：
Kondoh, Azusa [1 ]
Kato, Takuro [2 ]
Chen, Hao [2 ]
Terada, Masahiro [2 ]
机构：
[1] Tohoku Univ, Res & Analyt Ctr Giant Mol, Grad Sch Sci, Sendai 9808578, Japan
[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai 9808578, Japan
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 30期
关键词：
D O I：
10.1021/acs.orglett.4c02532
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective addition reaction of alkynyl esters with imines was developed under asymmetric autotandem catalysis with a chiral Br & oslash;nsted base. A chiral bis(guanidino)iminophosphorane organosuperbase, which has much higher basicity than that of conventional chiral organic bases, efficiently promoted both the intramolecular cyclization for the construction of a benzofuran ring or a benzothiophene ring and the sequential enantioselective direct Mannich-type reaction of diarylmethane derivatives, affording enantio-enriched diarylalkane derivatives that are otherwise difficult to access.
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页码：6523 / 6528
页数：6
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共 38 条
  • [1] Pd-Catalyzed Rearrangement of N-Alloc-N-allyl Ynamides via Auto-Tandem Catalysis: Evidence for Reversible C-N Activation and Pd(0)-Accelerated Ketenimine Aza-Claisen Rearrangement
    Alexander, Juliana R.
    Shchepetkina, Veronika, I
    Stankevich, Ksenia S.
    Benedict, Rory J.
    Bernhard, Samuel P.
    Dreiling, Reagan J.
    Cook, Matthew J.
    [J]. ORGANIC LETTERS, 2021, 23 (02) : 559 - 564
  • [2] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION
    BORDWELL, FG
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) : 456 - 463
  • [3] ACIDITIES OF THE H-C PROTONS IN CARBOXYLIC ESTERS, AMIDES, AND NITRILES
    BORDWELL, FG
    FRIED, HE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) : 4327 - 4331
  • [4] Auto-Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst
    Camp, Jason E.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (03) : 425 - 433
  • [5] Formal nucleophilic pyrrolylmethylation via palladium-based auto-tandem catalysis: switchable regiodivergent synthesis and remote chirality transfer
    Chen, Zhi
    Li, Yu-Fan
    Tan, Shun-Zhong
    Ouyang, Qin
    Chen, Zhi-Chao
    Du, Wei
    Chen, Ying-Chun
    [J]. CHEMICAL SCIENCE, 2022, 13 (42) : 12433 - 12439
  • [6] Das S., 2021, ORGANOSUPERBASE ANGE, V60, P1417, DOI [10.1002/anie.202012492, DOI 10.1002/ANIE.202012492]
  • [7] Enantioselective direct Michael addition of cyanohydrin ether derivatives to enones catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase
    Das, Saikat
    Kondoh, Azusa
    Terada, Masahiro
    [J]. CHEMICAL SCIENCE, 2023, 14 (12) : 3154 - 3159
  • [8] Chiral guanidines and their derivatives in asymmetric synthesis
    Dong, Shunxi
    Feng, Xiaoming
    Liu, Xiaohua
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (23) : 8525 - 8540
  • [9] Tandem catalysis: a taxonomy and illustrative review
    Fogg, DE
    dos Santos, EN
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2365 - 2379
  • [10] Thiourea-Tertiary Amine Promoted Cascade Catalysis: A Tool for Complexity Generation
    Gandhi, Soniya
    Sivadas, Vishnudas
    Baire, Beeraiah
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (02) : 220 - 234
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