Unusual and unexpected reactivity of t-butyl dicarbonate (Boc2O)with alcohols in the presence of magnesium perchlorate.: A new and general route to t-butyl ethers

被引:73
作者
Bartoli, G [1 ]
Bosco, M [1 ]
Locatelli, M [1 ]
Marcantoni, E [1 ]
Melchiorre, P [1 ]
Sambri, L [1 ]
机构
[1] Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
关键词
D O I
10.1021/ol047704o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new mild method for protecting alcohols as t-butyl ethers is reported. The reaction proceeds with Mg(ClO4)(2) and Boc(2)O and shows general applicability. The deprotection of t-butyl ethers has also been revisited. Preliminary results indicate the CeCl3.7H(2)O/Nal system is a very suitable catalyst for their removal.
引用
收藏
页码:427 / 430
页数:4
相关论文
共 23 条
  • [1] A Lewis acid-mediated protocol for the protection of aryl amines as their Boc-derivatives
    Bartoli, G
    Bosco, M
    Locatelli, M
    Marcantoni, E
    Massaccesi, M
    Melchiorre, P
    Sambri, L
    [J]. SYNLETT, 2004, (10) : 1794 - 1798
  • [2] Zn(ClO4)2•6H2O as a powerful catalyst for the conversion of β-ketoesters into β-enamino esters
    Bartoli, G
    Bosco, M
    Locatelli, M
    Marcantoni, E
    Melchiorre, P
    Sambri, L
    [J]. SYNLETT, 2004, (02) : 239 - 242
  • [3] Zn(ClO4)2•6H2O as a powerful catalyst for a practical acylation of alcohols with acid anhydrides
    Bartoli, G
    Bosco, M
    Dalpozzo, R
    Marcantoni, E
    Massaccesi, M
    Sambri, L
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) : 4611 - 4617
  • [4] The CeCl3•nH2O/NaI system in organic synthesis:: An efficient water tolerant Lewis acid promoter
    Bartoli, G
    Marcantoni, E
    Sambri, L
    [J]. SYNLETT, 2003, (14) : 2101 - 2116
  • [5] Bartoli G, 2003, SYNLETT, P39
  • [6] LiClO4-acyl anhydrides complexes as powerful acylating reagents of aromatic compounds in solvent free conditions
    Bartoli, G
    Bosco, M
    Marcantoni, E
    Massaccesi, M
    Rinaldi, S
    Sambri, L
    [J]. TETRAHEDRON LETTERS, 2002, 43 (36) : 6331 - 6333
  • [7] Bartoli G, 2001, SYNLETT, P1897
  • [8] Bartoli G, 1998, SYNLETT, P209
  • [9] BARTOLI G, 2005, IN PRESS ADV SYNTH C
  • [10] Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited.: Their reactions with amines and alcohols
    Basel, Y
    Hassner, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) : 6368 - 6380