Facile synthesis of 3,3-diallyl isoindolones via a indium-mediated double allylation of ortho-cyanobenzoates

被引：22
作者：
Kim, Sung Hwan
Kim, Se Hee
Kim, Ko Hoon
Kim, Jae Nyoung [1 ]
机构：
[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 05期
关键词：
Isoindolones; Indium; Barbier reaction; Double allylation; ortho-Cyanobenzoates; ALPHA-HOMOALLYLIC ALCOHOLS; AQUEOUS-MEDIA; ASYMMETRIC-SYNTHESIS; MECHANISTIC PROPOSAL; ADDITION-REACTIONS; ORGANIC-REACTIONS; BARBIER REACTION; NITRILES; REAGENTS; ISOINDOLINONES;
D O I：
10.1016/j.tetlet.2009.12.034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Various 3,3-diallyl isoindolones were synthesized via a indium-mediated Barbier type double allylation reaction of ortho-cyanobenzoates in good yields in short time. The reactivity of nitrile group toward allylindium is sufficient to form a cyclic compound when a suitable electrophilic center is present in the same molecule to trap the imine intermediate. (c) 2009 Elsevier Ltd. All rights reserved.
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收藏
页码：860 / 862
页数：3
相关论文
共 42 条
[1]   PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS [J].
ARAKI, S ;
SHIMIZU, T ;
JOHAR, PS ;
JIN, SJ ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2538-2542
[2]   Recent advances in indium-promoted organic reactions [J].
Auge, Jacques ;
Lubin-Germain, Nadege ;
Uziel, Jacques .
SYNTHESIS-STUTTGART, 2007, (12) :1739-1764
[3]   Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones.: Part 2:: N-acyliminium ion cyclisations with an internal alkene nucleophile [J].
Bahajaj, AA ;
Vernon, JM ;
Wilson, GD .
TETRAHEDRON, 2004, 60 (05) :1247-1253
[4]   A direct synthesis of 1-aryl- and 1-alkenylcyclopropylamines from aryl and alkenyl nitriles [J].
Bertus, P ;
Szymoniak, J .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7133-7136
[5]   Diene-titanium complexes as synthetic intermediates for the construction of three- or five-membered carbocycles [J].
Bertus, Philippe ;
Menant, Christine ;
Tanguy, Chloe ;
Szymoniak, Jan .
ORGANIC LETTERS, 2008, 10 (05) :777-780
[6]   Addition of transiently-generated methyl o-lithiobenzoate to imines. An isoindolone annulation [J].
Campbell, JB ;
Dedinas, RF ;
TrumbowerWalsh, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6205-6211
[7]   Asymmetric synthesis of 3-substituted isoindolinones: Application to the total synthesis of (+)-lennoxamine [J].
Comins, DL ;
Schilling, S ;
Zhang, YC .
ORGANIC LETTERS, 2005, 7 (01) :95-98
[8]   Tandem conjugate cyanide addition-Dieckmann condensation in the synthesis of the ABCD-ring system of lactonamycin [J].
Deville, JP ;
Behar, V .
ORGANIC LETTERS, 2002, 4 (08) :1403-1405
[9]   Asymmetric synthesis of 3-aryl-substituted 2,3-dihydro-1H-isoindol-1-ones [J].
Enders, D ;
Braig, V ;
Raabe, G .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (11) :1528-1535
[10]   Effect of substitution on novel tricyclic HIV-1 integrase inhibitors [J].
Fardis, Maria ;
Jin, Haolun ;
Jabri, Salman ;
Cai, Ruby Z. ;
Mish, Michael ;
Tsiang, Manuel ;
Kim, Choung U. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (15) :4031-4035
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