An oxathiaphospholane approach to one-pot phosphorothioylation of isoprenoid alcohols

被引：6
|
作者：
Zmudzka, K
Nawrot, B
Chojnacki, T
Stec, WJ
机构：
[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Bioorgan Chem, PL-90363 Lodz, Poland
[2] Polish Acad Sci, Inst Biochem & Biophys, PL-02106 Warsaw, Poland
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 09期
关键词：
D O I：
10.1021/ol049771o
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Allyl, isopentenyl, geranyl, citronellyl, farnesyl, and phytyl alcohols were transformed in good yield (>60%) into their phosphorothioates via a DBU-assisted 1,3,2-oxathiaphospholane ring-opening condensation with 2-(2-cyanoethoxy)-2-thiono-1,3,2-oxathiaphospholane, a reagent that is stable and easy to handle, followed by subsequent removal of the 2-cyanoethyl group from the intermediate phosphorothioate diester under basic conditions.
引用
收藏
页码：1385 / 1387
页数：3
相关论文
共 50 条
  • [1] Oxathiaphospholane approach to N- and O-phosphorothioylation of amino acids
    Baraniak, J
    Kaczmarek, R
    Korczynski, D
    Wasilewska, E
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21): : 7267 - 7274
  • [2] One-pot synthesis of cage alcohols
    Yu. N. Klimochkin
    A. V. Yudashkin
    E. O. Zhilkina
    E. A. Ivleva
    I. K. Moiseev
    Ya. F. Oshis
    Russian Journal of Organic Chemistry, 2017, 53 : 971 - 976
  • [3] One-pot synthesis of cage alcohols
    Klimochkin, Yu. N.
    Yudashkin, A. V.
    Zhilkina, E. O.
    Ivleva, E. A.
    Moiseev, I. K.
    Oshis, Ya. F.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (07) : 971 - 976
  • [4] One-pot Approach to the Conversion of Alcohols into α-Halo-α, β-unsaturated Esters
    Gui Sheng DENG?
    Chinese Chemical Letters, 2006, (03) : 329 - 332
  • [5] One-Pot Approach to the Conversion of Alcohols into α-Iodo-α,β-unsaturated Esters
    Karama, Usama
    SYNTHETIC COMMUNICATIONS, 2010, 40 (23) : 3447 - 3451
  • [6] One-pot tandem approach for the synthesis of benzimidazoles and benzothiazoles from alcohols
    Raghavendra, Goravanahalli M.
    Ramesha, Ajjahalli B.
    Revanna, Cigalli N.
    Nandeesh, Kebbahalli N.
    Mantelingu, Kempegowda
    Rangappa, Kanchugarakoppal S.
    TETRAHEDRON LETTERS, 2011, 52 (43) : 5571 - 5574
  • [7] One-pot approach to the conversion of alcohols into α-halo-α, β-unsaturated esters
    Deng, GS
    Liu, CY
    CHINESE CHEMICAL LETTERS, 2006, 17 (03) : 329 - 332
  • [8] Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols
    Casnati, Alessandra
    Lichosyt, Dawid
    Lainer, Bruno
    Veth, Lukas
    Dydio, Pawel
    ORGANIC LETTERS, 2021, 23 (09) : 3502 - 3506
  • [9] Simple One-Pot Conversion of Alcohols into Nitriles
    Shimojo, Hiroyuki
    Moriyama, Katsuhiko
    Togo, Hideo
    SYNTHESIS-STUTTGART, 2013, 45 (15): : 2155 - 2164
  • [10] One-Pot Synthesis of Isocyanides from Alcohols
    Okada, Iku
    Kitano, Yoshikazu
    SYNTHESIS-STUTTGART, 2011, (24): : 3997 - 4002
12345