A NOVEL PALLADIUM-CATALYZED DEOXYGENATION OF ENEDIOLS TO 1,3-DIENES

被引：0
|
作者：
TROST, BM [1 ]
TOMETZKI, GB [1 ]
机构：
[1] STANFORD UNIV, STANFORD, CA 94305 USA
来源：
SYNTHESIS-STUTTGART | 1991年 / 12期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hydroxylative Knoevenagel condensation of aldehydes followed by reduction provides a simple entry to 1,4-enediols. Subjecting the dicarbonate to a palladium(0) catalyst in the presence of triisopropyl phosphite achieves a, mild vinylogous deoxygenation to (E)-1,3-dienes. Stereocontrolled synthesis of the sex pheromone of the red bollworm moth, (E)-9,11-dodecadienyl acetate, and a formal synthesis of the cotton boll weevil antifeedant, alpha-eleostearic acid, demonstrate the utility of this new methodology.
引用
收藏
页码：1235 / 1245
页数：11
相关论文
共 50 条
  • [21] Palladium-Catalyzed Allylation of Cyclopropyl Acetylenes with Oxindoles to Construct 1,3-Dienes
    Lu, Chuan-Jun
    Yu, Xin
    Chen, Yu-Ting
    Song, Qing-Bao
    Yang, Zhen-Ping
    Wang, Hong
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (06) : 680 - 688
  • [22] Palladium-catalyzed hydroamination of 1,3-dienes:: A colorimetric assay and enantioselective additions
    Löber, O
    Kawatsura, M
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) : 4366 - 4367
  • [23] On the nature of the palladium-catalyzed elimination of allylic carbonates to form 1,3-dienes
    Takacs, JM
    Lawson, EC
    Clement, F
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 633 - ORGN
  • [24] Ligand control of regioselectivity in palladium-catalyzed heteroannulation reactions of 1,3-Dienes
    Rodina, Dasha
    Vaith, Jakub
    Paradine, Shauna M.
    [J]. NATURE COMMUNICATIONS, 2024, 15 (01)
  • [25] PALLADIUM-CATALYZED DIMERIZATION DOUBLE STANNATION OF 1,3-DIENES USING HEXAMETHYLDISTANNANE
    TSUJI, Y
    KAKEHI, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (14) : 1000 - 1001
  • [26] PALLADIUM-CATALYZED REACTIONS OF 1,3-DIENES WITH ACTIVE METHYLENE COMPOUNDS - ORGN
    HATA, G
    TAKAHASH.K
    MIYAKE, A
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1970, (SEP): : 112 - &
  • [27] Photoinduced, Palladium-Catalyzed Enantioselective 1,2-Alkylsulfonylation of 1,3-Dienes
    Liu, Zhi-Lin
    Ye, Zhi-Peng
    Liao, Zi-hao
    Lu, Wei-Dong
    Guan, Jian-Ping
    Gao, Zi-Yi
    Chen, Kai
    Chen, Xiao-Qing
    Xiang, Hao-Yue
    Yang, Hua
    [J]. ACS CATALYSIS, 2024, 14 (05) : 3725 - 3732
  • [28] STEREOSELECTIVE AND REGIOSELECTIVE PALLADIUM-CATALYZED 1,4-DIACETOXYLATION OF 1,3-DIENES
    BACKVALL, JE
    BYSTROM, SE
    NORDBERG, RE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24): : 4619 - 4631
  • [29] Palladium-catalyzed 1,2-selective intermolecular arylamination of 1,3-dienes
    Li, Zhuo-Mei
    Zhang, Zhe
    Li, Xue-Song
    Jiao, Rui-Qiang
    Chen, Xi
    Liu, Xue-Yuan
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2024,
  • [30] FACILE ROUTE TO 1-PHOSPHORYL-1,3-DIENES AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES
    AKERMARK, B
    NYSTROM, JE
    REIN, T
    BACKVALL, JE
    HELQUIST, P
    ASLANIAN, R
    [J]. TETRAHEDRON LETTERS, 1984, 25 (50) : 5719 - 5722
12345