Diastereoselective Passerini Reaction of Biobased Chiral Aldehydes: Divergent Synthesis of Various Polyfunctionalized Heterocycles

被引：31
|
作者：
Moni, Lisa [1 ]
Banfi, Luca [1 ]
Basso, Andrea [1 ]
Martino, Elisa [1 ]
Riva, Renata [1 ]
机构：
[1] Univ Genoa, Dept Chem & Ind Chem, Via Dodecaneso 31, I-16146 Genoa, Italy
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 07期
关键词：
UGI MULTICOMPONENT REACTION; FUNCTIONAL-GROUPS; ACID; PYRROLIDINES; DERIVATIVES; ERYTHRITOL; VERSATILE; ALCOHOLS; SEQUENCE;
D O I：
10.1021/acs.orglett.6b00487
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lewis acid catalyzed Passerini reactions on chiral aldehydes derived from desymmetrized erythritol take place with unprecedented diastereoselectivity. The resulting adducts have been selectively and efficiently converted into a variety of densely functionalized, polyoxygenated heterocycles.
引用
收藏
页码：1638 / 1641
页数：4
相关论文
共 27 条
  • [1] Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction
    Forconesi, Gabriella Vitali
    Banfi, Luca
    Basso, Andrea
    Lambruschini, Chiara
    Moni, Lisa
    Riva, Renata
    MOLECULES, 2020, 25 (14):
  • [2] Synthesis of photoresponsive biobased adhesive polymers via the Passerini three-component reaction
    Chou, Li-Chieh
    Matsubara, Kiho
    Takada, Kenji
    Kaneko, Tatsuo
    Kakuchi, Ryohei
    POLYMER JOURNAL, 2023, 55 (10) : 1067 - 1074
  • [3] DTBP-promoted Passerini-type reaction of isocyanides with aldehydes: Synthesis of α-acyloxycarboxamides
    Wang, Zhuo
    Zhang, Yan
    Wu, Zi-Han
    Zhao, Yu-Long
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2022, 69 (10) : 1794 - 1802
  • [4] Ugi and Passerini Reactions of Biocatalytically Derived Chiral Aldehydes: Application to the Synthesis of Bicyclic Pyrrolidines and of Antiviral Agent Telaprevir
    Moni, Lisa
    Banfi, Luca
    Basso, Andrea
    Carcone, Luca
    Rasparini, Marcello
    Riva, Renata
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (07) : 3411 - 3428
  • [5] Divergent and Diastereoselective Synthesis of α-Monosubstituted and trans-α,β-Disubstituted γ-Lactams from (S)-N,N-Dibenzyl-α-amino Aldehydes via Henry and Michael Reactions
    Meirelis, Francine P.
    Vieira, Bruna G. N.
    Pereira, Vera L. P.
    SYNTHESIS-STUTTGART, 2020, 52 (23): : 3650 - 3656
  • [6] Diastereoselective synthesis of β-lactams via Kinugasa reaction of acyclic chiral nitrones
    Mucha, Lukasz
    Parda, Kamil
    Staszewska-Krajewska, Olga
    Stecko, Sebastian
    Ulikowski, Artur
    Frelek, Jadwiga
    Suszczynska, Agata
    Chmielewski, Marek
    Furman, Bartiomiej
    TETRAHEDRON-ASYMMETRY, 2016, 27 (01) : 12 - 21
  • [7] Diastereoselective synthesis of chiral β-amino-α-hydroxy-H-phosphinates through hydrophosphinylation of α-amino aldehydes
    Yamagishi, T
    Suemune, K
    Yokomatsu, T
    Shibuya, S
    TETRAHEDRON LETTERS, 2001, 42 (30) : 5033 - 5036
  • [8] Diastereoselective addition of functionalized organolithium compounds to (-)-menthone - synthesis of chiral ligands for enantioselective addition of diethylzinc to aldehydes
    Zagranyarska, I.
    Kostova, K.
    Chimov, A.
    Dimitrov, V.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2017, 49 : 10 - 17
  • [9] Copper(I) Halide Promoted Diastereoselective Synthesis of Chiral Propargylamines and Chiral Allenes using 2-Dialkylaminomethylpyrrolidine, Aldehydes, and 1-Alkynes
    Gurubrahamam, Ramani
    Periasamy, Mariappan
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (04) : 1463 - 1470
  • [10] Diastereoselective Synthesis of γ-Lactones through Reaction of Sulfoxonium Ylides, Aldehydes, and Ketenes: Substrate Scope and Mechanistic Studies
    Peraino, Nicholas J.
    Mondal, Mukulesh
    Ho, Han-Jen
    Beuque, Antoine
    Viola, Evan
    Gary, Melanie
    Wheeler, Kraig A.
    Kerrigan, Nessan J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (01) : 151 - 160
123