wFeCl3-Catalyzed Intramolecular Michael Reaction of Styrenes for the Synthesis of Highly Substituted Indenes

被引：19

作者：

Dethe, Dattatraya H. ^{[1
]}

Murhade, Ganesh M. ^{[1
]}

Ghosh, Sourav ^{[1
]}

机构：

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 16期

关键词：

CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED KETONES; STILBENE DERIVATIVES; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; SIMPLE ALKENES; CYCLIZATION; ALDEHYDES; CATALYST; INHIBITORS;

D O I：

10.1021/acs.joc.5b01071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intramolecular FeCl3-catalyzed Michael addition reaction of styrene, a poor nudeophile, onto alpha,beta-unsaturated ketones was developed for the synthesis of highly substituted indene derivatives. The method was further applied to the total synthesis of the sesquiterpene natural products (+/-)-jungianol and 1-epi-jungianol.

引用

页码：8367 / 8376

页数：10

共 72 条

[11] Indenyl complexes of Group 8 metals [J].

Cadierno, V ;

Diez, J ;

Gamasa, MP ;

Gimeno, J ;

Lastra, E .

COORDINATION CHEMISTRY REVIEWS, 1999, 193-5 :147-205

[12] Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes [J].

Chang, KJ ;

Rayabarapu, DK ;

Cheng, CH .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) :4781-4787

[13] A 1,3-carbonyl shift in the platinum-catalyzed aromatization of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes [J].

Chaudhuri, Rupsha ;

Das, Arindam ;

Liao, Hsin-Yi ;

Liu, Rai-Shung .

CHEMICAL COMMUNICATIONS, 2010, 46 (25) :4601-4603

[14] Diphenylprolinol methyl ether: A highly enantioselective catalyst for Michael addition of aldehydes to simple enones [J].

Chi, YG ;

Gellman, SH .

ORGANIC LETTERS, 2005, 7 (19) :4253-4256

[15] Differential response of estrogen receptor subtypes to 1,3-diarylindene and 2,3-diarylindene ligands [J].

Clegg, NJ ;

Paruthiyil, S ;

Leitman, DC ;

Scanlan, TS .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (19) :5989-6003

[16] Michael additions catalyzed by transition metals and lanthanide species.: A review [J].

Comelles, J ;

Moreno-Mañas, M ;

Vallribera, A .

ARKIVOC, 2005, :207-238

[17] Lewis acid catalyzed Nazarov type cyclization for the synthesis of a substituted indane framework: total synthesis of (±)-mutisianthol [J].

Dethe, Dattatraya H. ;

Boda, Raghavender ;

Murhade, Ganesh M. .

Organic Chemistry Frontiers, 2015, 2 (06) :645-648

[18] FeCl3 mediated intramolecular olefin-cation cyclization of cinnamates for the synthesis of highly substituted indenes [J].

Dethe, Dattatraya H. ;

Murhade, Ganesh M. .

CHEMICAL COMMUNICATIONS, 2013, 49 (73) :8051-8053

[19] FeCl3 Catalyzed Prins-Type Cyclization for the Synthesis of Highly Substituted Indenes: Application to the Total Synthesis of (±)-Jungianol and epi-Jungianol [J].

Dethe, Dattatraya H. ;

Murhade, Ganesh .

ORGANIC LETTERS, 2013, 15 (03) :429-431

[20] Expanding the scope of Lewis acid catalysis in water:: Remarkable ligand acceleration of aqueous ytterbium triflate catalyzed Michael addition reactions [J].

Ding, R ;

Katebzadeh, K ;

Roman, L ;

Bergquist, KE ;

Lindström, UM .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :352-355

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