1,2,4-Trioxepanes: Redox-cleavable protection for carbonyl groups

被引:22
作者
Ahmed, A [1 ]
Dussault, PH [1 ]
机构
[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA
关键词
D O I
10.1021/ol048484h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2,4-trioxepanes, readily prepared and easily handled derivatives of aldehydes and ketones, are stable to a variety of synthetic conditions and yet easily deblocked with Zn/HOAc or Mg/MeOH to regenerate the parent carbonyl. Trioxepanes may provide an alternative to 1,3-dithianes for acid-stable protection of carbonyl groups.
引用
收藏
页码:3609 / 3611
页数:3
相关论文
共 10 条
[1]   Magnesium/methanol: Sn effective reducing agent for peroxides [J].
Dai, P ;
Dussault, PH ;
Trullinger, TK .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2851-2852
[2]   NOVEL METHOD FOR THE PREPARATION OF TRIETHYLSILYL PEROXIDES FROM OLEFINS BY THE REACTION WITH MOLECULAR-OXYGEN AND TRIETHYLSILANE CATALYZED BY BIS(1,3-DIKETONATO)COBALT(II) [J].
ISAYAMA, S ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1989, (04) :573-576
[3]   Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols [J].
Ito, T ;
Tokuyasu, T ;
Masuyama, A ;
Nojima, M ;
McCullough, KJ .
TETRAHEDRON, 2003, 59 (04) :525-536
[4]   DISPIRO-1,2,4-TRIOXANES AS PRECURSORS OF MEDIUM RING LACTONES - THERMOLYSIS OF INDAN-2-SPIRO-3'-(1',2',4'-TRIOXANE)-6'-SPIRO-1''-CYCLOHEXANE [J].
KERR, B ;
MCCULLOUGH, KJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (09) :590-592
[5]  
KROPF H, 1988, METHODS ORGANIC CHEM, V13, P1968
[6]   Co(thd)2:: a superior catalyst for aerobic epoxidation and hydroperoxysilylation of unactivated alkenes:: application to the synthesis of spiro-1,2,4-trioxanes [J].
O'Neill, PM ;
Hindley, S ;
Pugh, MD ;
Davies, J ;
Bray, PG ;
Park, BK ;
Kapu, DS ;
Ward, SA ;
Stocks, PA .
TETRAHEDRON LETTERS, 2003, 44 (44) :8135-8138
[7]   Regioselective Mukaiyama hydroperoxysilylation of 2-alkyl- or 2-aryl-prop-2-en-1-ols: application to a new synthesis of 1,2,4-trioxanes [J].
O'Neill, PM ;
Pugh, M ;
Davies, J ;
Ward, SA ;
Park, BK .
TETRAHEDRON LETTERS, 2001, 42 (27) :4569-4571
[8]   A convenient synthesis of substituted 1,2,4-trioxepanes via Co(II) catalyzed oxygenation of cinnamyl alcohol [J].
Oh, CH ;
Kang, JH .
TETRAHEDRON LETTERS, 1998, 39 (18) :2771-2774
[9]   SYNTHESIS AND REACTIONS OF BETA-HYDROXYHYDROPEROXIDES [J].
SUBRAMANYAM, V ;
BRIZUELA, CL ;
SOLOWAY, AH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (13) :508-509
[10]   Co(III)-alkyl complex- and Co(III)-alkylperoxo complex-catalyzed triethylsilylperoxidation of alkenes with molecular oxygen and triethylsilane [J].
Tokuyasu, T ;
Kunikawa, S ;
Masuyama, A ;
Nojima, M .
ORGANIC LETTERS, 2002, 4 (21) :3595-3598