REGIOSELECTIVE AND STEREOSELECTIVE, DDQ-INDUCED OXIDATIVE COUPLING OF ISOCHROMANS AND ISOTHIOCHROMAN WITH ALCOHOLS

被引:40
|
作者
XU, YC
LEBEAU, E
GILLARD, JW
ATTARDO, G
机构
[1] BioChem Pharma Inc., Laval, Que. H7V 1B7
关键词
D O I
10.1016/S0040-4039(00)79242-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) induced oxidative coupling of isochromans or isothiochroman and alcohols proceeds in high yield with good regio- and stereochemical control.
引用
收藏
页码:3841 / 3844
页数:4
相关论文
共 10 条
  • [1] DDQ-INDUCED AND STEREOSELECTIVE FUNCTIONALIZATION AT HETEROSUBSTITUTED BENZYLIC POSITIONS BY CARBON NUCLEOPHILES
    XU, YC
    ROY, C
    LEBEAU, E
    TETRAHEDRON LETTERS, 1993, 34 (51) : 8189 - 8192
  • [2] Stereoselective, oxidative C-C bond coupling of naphthopyran induced by DDQ: Stereocontrolled total synthesis of deoxyfrenolicin
    Xu, YC
    Kohlman, DT
    Liang, SX
    Erikkson, C
    ORGANIC LETTERS, 1999, 1 (10) : 1599 - 1602
  • [3] Enantioselective total synthesis of deoxyfrenolicin and related pyranonaphthoquinone natural products via DDQ-induced, stereoselective C-C bond coupling of naphthopyrans with carbon nucleophiles.
    Xu, YC
    Kohlman, DT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U180 - U180
  • [4] The regioselective coupling of 2-arylquinazolinone C-H with aldehydes and benzyl alcohols under oxidative conditions
    Kshirsagar, Umesh A.
    Waghmare, Deepali S.
    Tambe, Shrikant D.
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (39) : 16697 - 16701
  • [5] Metal-dependent regioselective oxidative coupling of 5,10,15-triarylporphyrins with DDQ-Sc(OTf)3 and formation of an oxo-quinoidal porphyrin
    Kamo, M
    Tsuda, A
    Nakamura, Y
    Aratani, N
    Furukawa, K
    Kato, T
    Osuka, A
    ORGANIC LETTERS, 2003, 5 (12) : 2079 - 2082
  • [6] BASE-INDUCED REARRANGEMENT OF 1-(TRIMETHYLSILYL)ALLYLIC ALCOHOLS - STEREOSELECTIVE AND REGIOSELECTIVE SYNTHESIS OF SILYL ENOL ETHERS THROUGH LITHIUM HOMOENOLATES
    KATO, M
    MORI, A
    OSHINO, H
    ENDA, J
    KOBAYASHI, K
    KUWAJIMA, I
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) : 1773 - 1778
  • [7] Palladium-Catalyzed Aerobic Oxidative Coupling of ortho-(Alkynyl)styrenes with Allylic Alcohols via 6-endo-dig Cyclization: Regioselective Construction of Polysubstituted Naphthalenes
    Ramesh, Perla
    Satyanarayana, Gedu
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 12856 - 12870
  • [8] Oxidative cross-dehydrogenative coupling (CDC) -H bond functionalization:butyl peroxybenzoate (TBPB)-promoted regioselective direct C-3 acylation/benzoylation of 2-indazoles with aldehydes/benzyl alcohols/styrenes
    Sharma, Richa
    Yadav, Lalit
    Yadav, Ravi Kant
    Chaudhary, Sandeep
    RSC ADVANCES, 2021, 11 (23) : 14178 - 14192
  • [9] I2 and aqueous TBHP induced aerial oxidative coupling of 2-aminobenzyl alcohols and nitriles: A novel metal-free route towards quinazolines synthesis
    Chetia, Swadhin
    Nath, Dipankar
    Purkayastha, Siddhartha K.
    Guha, Ankur K.
    Sarma, Diganta
    TETRAHEDRON LETTERS, 2024, 142
  • [10] Radical-Induced Metal and Solvent-Free Cross-Coupling Using TBAI-TBHP: Oxidative Amidation of Aldehydes and Alcohols with N-Chloramines via C-H Activation
    Achar, Tapas Kumar
    Mal, Prasenjit
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 666 - 672