Synthesis of 3-oxoalkylphosphonates via the conjugate addition of acylcuprates to diethyl vinylphosphonate

被引：11
|
作者：
Li, NS
Yu, S
Kabalka, GW [1 ]
机构：
[1] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA
[2] Univ Tennessee, Dept Radiol, Knoxville, TN 37996 USA
来源：
ORGANOMETALLICS | 1999年 / 18卷 / 09期
关键词：
D O I：
10.1021/om980995i
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Acylcuprate reagents generated by the reaction of dialkylcyanocuprates with carbon monoxide at low temperature (-110 degrees C) readily react with diethyl vinylphosphonate to give 3-oxoalkylphosphonates in good yields after hydrolysis. The reaction intermediates can also be trapped by allylic bromides to give 1-allyl-3-oxo-alkylphosphonates in good yields.
引用
收藏
页码：1811 / 1814
页数：4
相关论文
共 50 条
  • [31] Total Synthesis of (R)-Sarkomycin via Asymmetric Rhodium-Catalyzed Conjugate Addition
    Westmeier, Johannes
    Kress, Steffen
    Pfaff, Christopher
    von Zezschwitz, Paultheo
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21): : 10718 - 10723
  • [32] Efficient synthesis of polyethylene glycol mono-carboxylate via Michael conjugate addition
    Chen, QQ
    Gabathuler, R
    SYNTHETIC COMMUNICATIONS, 2004, 34 (13) : 2425 - 2432
  • [33] Highly Enantioselective Synthesis of Nitrocyclopropanes via Organocatalytic Conjugate Addition of Bromomalonate to α,β-Unsaturated Nitroalkenes
    Xuan, Yi-ning
    Nie, Shao-zhen
    Dong, Li-ting
    Zhang, Jun-min
    Yan, Ming
    ORGANIC LETTERS, 2009, 11 (07) : 1583 - 1586
  • [34] Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition
    Davies, Stephen G.
    Garner, A. Christopher
    Goddard, Euan C.
    Kruchinin, Dennis
    Roberts, Paul M.
    Smith, Andrew D.
    Rodriguez-Solla, Humberto
    Thomson, James E.
    Toms, Steven M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (12) : 1961 - 1969
  • [35] A stereoselective synthesis of a (3S,4S)-3-aminodeoxystatine derivative via an intramolecular conjugate addition.
    Kim, YG
    Yoo, D
    Min, GH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U198 - U198
  • [36] Synthesis of chiral tetronic acid derivatives via organocatalytic conjugate addition of ethyl 4-chloro-3-oxobutanoate to nitroalkenes
    Yan, Yun-yun
    Lu, Rui-jiong
    Wang, Jin-jia
    Xuan, Yi-ning
    Yan, Ming
    TETRAHEDRON, 2012, 68 (31) : 6123 - 6130
  • [37] Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindoles via a 1,6-conjugate addition reaction
    Rahman, Abdul
    Zhou, Qiaoxia
    Lin, Xufeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (29) : 5301 - 5309
  • [38] SYNTHESIS OF HYDROXYLATED STEROID-HORMONES VIA CONJUGATE ADDITION OF A SILYL-CUPRATE REAGENT
    GARSIDE, D
    KIRK, DN
    WALDRON, NM
    STEROIDS, 1994, 59 (12) : 702 - 711
  • [39] ASYMMETRIC SYNTHESIS OF β-LACTAMS BY INTRAMOLECULAR CONJUGATE ADDITION OF SERINE AND CYSTEINE DERIVATIVES VIA MEMORY OF CHIRALITY
    Hyakutake, Ryuichi
    Yoshimura, Tomoyuki
    Ueda, Yoshihiro
    Hayashi, Kazuhiro
    Furuta, Takumi
    Kawabata, Takeo
    HETEROCYCLES, 2018, 97 (02) : 1128 - 1147
  • [40] Total synthesis of clavosolide A via tandem allylic oxidation/oxa-conjugate addition reaction
    Baker, Joseph B.
    Kim, Hyoungsu
    Hong, Jiyong
    TETRAHEDRON LETTERS, 2015, 56 (23) : 3120 - 3122
12345