Intramolecular tandem Michael-type addition/aldol cyclization induced by TiCl4-R4NX combinations

被引：51
|
作者：
Yagi, K [1 ]
Turitani, T [1 ]
Shinokubo, H [1 ]
Oshima, K [1 ]
机构：
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 18期
关键词：
D O I：
10.1021/ol026413h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Treatment of formyl alpha,beta-enones with a TiCl4-R4NX combination induces an intramolecular aldol cyclization to furnish 2-acyl-3-halocyclohexanol with three controlled consecutive stereogenic centers. The reaction of bis-alpha,beta-enones with the combination provides cyclic diketones with high stereoselectivity via an intramolecular Michael addition reaction.
引用
收藏
页码：3111 / 3114
页数：4
相关论文
共 50 条
  • [21] Visible-light-induced tandem radical addition/cyclization of 2-alkenylphenols and CBr4 for the synthesis of 4-arylcoumarins
    Tan, Li-Ping
    Liang, Dong
    Cheng, Ying
    Xiao, Wen-Jing
    Chen, Jia-Rong
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (18) : 5052 - 5057
  • [22] An approach to anti-HIV-1 active Calophyllum coumarin synthesis:: An enantioselective construction of 2,3-dimethyl-4-chromanone ring by quinine-assisted intramolecular Michael-type addition
    Ishikawa, T
    Oku, Y
    Tanaka, T
    Kumamoto, T
    TETRAHEDRON LETTERS, 1999, 40 (19) : 3777 - 3780
  • [23] Tandem phospha-Michael addition/cyclization/dehydration of 2-hydroxychalcones with H-phosphine oxides for the synthesis of 4-phosphorylated 4H-chromenes
    Wen, Zhong
    Yang, Kai-Cheng
    Zheng, Shi-Lu
    Zhang, Yu-Shan
    Wang, Sheng-Jun
    Ni, Hai-Liang
    Chen, Long
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (45) : 9076 - 9081
  • [24] 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
  • [25] SYNTHESIS OF PURINES BY CYCLIZATION OF MICHAEL-TYPE ADDUCTS FROM 6-AMINOPYRIMIDINES AND "4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE
    YONEDA, F
    KAWAMURA, M
    MATSUMOTO, S
    HIGUCHI, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (20): : 2285 - 2288
  • [26] The Michael-type addition reaction:: A stereocontrolled construction of a new quaternary chiral center at C(2) of 2-(4-hydroxybenzyl)cyclohexanone derivatives
    Wimmer, Z
    Saman, D
    Kuldová, J
    Desmaële, D
    d'Angelo, J
    Goudey-Perrière, F
    HELVETICA CHIMICA ACTA, 1998, 81 (11) : 2017 - 2023
  • [27] Solvent effects on stereoselectivity in 2,3-dimethyl-4-chromanone cyclization by quinine-catalyzed asymmetric intramolecular oxo-Michael addition
    Tanaka, T
    Kumamoto, T
    Ishikawa, T
    TETRAHEDRON-ASYMMETRY, 2000, 11 (23) : 4633 - 4637
  • [28] Tandem retro-Michael addition-Claisen rearrangement-intramolecular cyclization: One-pot synthesis of densely functionalized ethyl dihydropyrimidine-4-carboxylates from simple building blocks
    Naidu, B. Narasimhulu
    SYNLETT, 2008, (04) : 547 - 550
  • [29] INTRAMOLECULAR CYCLIZATION OF NEROL AND THE RELATED ATTACK OF (Z)-ALLYLIC ALCOHOL MOIETY ON THE TERMINAL OLEFIN LINKAGE AS INDUCED BY TICL4-PHNHME COMPLEX - SYNTHESIS OF NEZUKONE
    ITOH, A
    SAITO, T
    OSHIMA, K
    NOZAKI, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (05) : 1456 - 1459
  • [30] Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction
    Yin, Guodong
    Fan, Ling
    Ren, Tianbing
    Zheng, Chunyang
    Tao, Qing
    Wu, Anxin
    She, Nengfang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (44) : 8877 - 8883
12345