Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars

被引：6
|
作者：
Berrocal, MV
Gil, MV
Román, E
Serrano, JA
Hursthouse, MB
Light, ME
机构：
[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain
[2] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 21期
关键词：
Michael addition; aldol cyclization; nitro compounds; sugars;
D O I：
10.1016/j.tetlet.2005.03.162
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The base-catalyzed Michael addition of primary nitro compounds derived from sugars with 2 equiv of methyl vinyl ketone or acrolein was followed, in situ, by an asymmetric intramolecular aldol cyclization, thus yielding 2-acyl-4-glyco-4-nitro-cyclohexanol derivatives with high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3673 / 3676
页数：4
相关论文
共 50 条
  • [31] Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition
    Cheng, Shuanghua
    Yu, Shouyun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (43) : 8607 - 8610
  • [32] Synthesis of Multifused Pyrrolo[1,2-a]quinoline Systems by Tandem Aza-Michael-Aldol Reactions and Their Application to Molecular Sensing Studies
    Bera, Anirban
    Azad, Sk Abulkalam
    Patra, Prasanta
    Sepay, Nayim
    Jana, Rathin
    Das, Tapas
    Saha, Amit
    Samanta, Shubhankar
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09): : 5622 - 5638
  • [33] ADDITION OF BROMINE TO CYCLOHEXYLIDENCYCLOHEXANE - SYNTHESIS OF 1,2-DIOXETHANES DERIVED FROM IT
    SALIDO, FP
    SASTRE, JAL
    AFINIDAD, 1987, 44 (409) : 269 - 272
  • [34] Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines
    Bhanja, Chittaranjan
    Jena, Satyaban
    Nayak, Sabita
    Mohapatra, Seetaram
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1668 - 1694
  • [35] Visible-Light-Induced Intramolecular Tandem Cyclization of Unactivated Indoloalkynes for the Synthesis of Sulfonylated and Selenylated Indolo[1,2-a]quinolines
    Zhang, Shouren
    Yuan, Jinwei
    Huang, Guangchao
    Ma, Chengjia
    Yang, Jingjing
    Yang, Liangru
    Xiao, Yongmei
    Qu, Lingbo
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11712 - 11727
  • [36] Synthesis of 1,2-Dihydroisoquinolines via Rhenium-catalyzed Tandem Cyclization and Nucleophilic Addition of 2-(1-Alkynyl)arylaldimines
    Umeda, Rui
    Ishida, Tetsuya
    Nakagawa, Yota
    Inoue, Mitsuru
    Yajima, Tatsuo
    Nishiyama, Yutaka
    CHEMISTRY LETTERS, 2018, 47 (06) : 753 - 755
  • [37] Tandem conjugate addition-aldol cyclization to give optically active 1-Aryl-1H-indenes via asymmetric Pd2+-catalyzed 1,4-addition of arylboronic acids
    Nishikata, Takashi
    Kobayashi, Yuri
    Kobayshi, Kenya
    Yamamoto, Yasunori
    Miyaura, Norio
    SYNLETT, 2007, (19) : 3055 - 3057
  • [38] MCPBA-Promoted Tandem Michael Addition-Intramolecular Cyclization of 2-Azido-β-amino Esters: Single Pot, Convenient Access to 1,2,4,5-Tetrasubstituted Imidazoles
    Raj, Raghu
    Hundal, M. S.
    Kumar, Vipan
    SYNLETT, 2014, 25 (14) : 2054 - 2058
  • [39] TANDEM INTRAMOLECULAR MICHAEL-ADDITION ALDOL CONDENSATION OR ACYLATION APPLIED TO D-GLUCOSE-DERIVED SUBSTRATES - PREPARATION OF ENANTIOMERIC OCTAHYDRONAPHTHALENONE DERIVATIVES EQUIPPED WITH C-FUNCTIONALITIES AND O-FUNCTIONALITIES
    TADANO, K
    NAGASHIMA, K
    UENO, Y
    OGAWA, S
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16): : 4496 - 4506
  • [40] TANDEM INTRAMOLECULAR MICHAEL ADDITION AND 1,3-DIPOLAR CYCLOADDITION REACTIONS OF OXIMES - VERSATILE NEW CARBON CARBON BOND FORMING METHODOLOGY
    ARMSTRONG, P
    GRIGG, R
    SURENDRAKUMAR, S
    WARNOCK, WJ
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (17) : 1327 - 1328
12345