Reductive metalation of 1,2-diaryl-substituted ethenes: synthetic applications

被引：17

作者：

Azzena, U ^{[1
]}

Dettori, G ^{[1
]}

Lubinu, C ^{[1
]}

Mannu, A ^{[1
]}

Pisano, L ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

TETRAHEDRON | 2005年 / 61卷 / 36期

关键词：

dicarbanions; stilbenes; metalation; reduction; cycloalkylation;

D O I：

10.1016/j.tet.2005.06.108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of 1,2-diaryl-substituted ethenes with Na metal in dry THF allowed easy access to a variety of 1,2-diaryl-1,2-disodiumethanes. These diorganometallic intermediates were elaborated into the corresponding 1,2-diarylethanes (aqueous work up), or cycloalkylated with 1,3-dichloropropanes. The last reaction led to a highly diastereoselective synthesis of trans-1,2-diaryl-substituted cyclopentanes. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8663 / 8668

页数：6

共 32 条

[1] Regioselective reductive demethoxylation of 3,4,5-trimethoxystilbenes [J].

Azzena, U ;

Dettori, G ;

Idini, MV ;

Pisano, L ;

Sechi, G .

TETRAHEDRON, 2003, 59 (40) :7961-7966

[2] REGIOSELECTIVE REDUCTIVE ELECTROPHILIC SUBSTITUTION OF DERIVATIVES OF 3,4,5-TRIMETHOXYBENZALDEHYDE [J].

AZZENA, U ;

MELLONI, G ;

PIRODDI, AM ;

AZARA, E ;

CONTINI, S ;

FENUDE, E .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :3101-3106

[3]

BAKER R, 1981, SYNTHESIS-STUTTGART, P117

[4] Palladium-catalyzed C-C coupling under thermomorphic conditions [J].

Bergbreiter, DE ;

Osburn, PL ;

Wilson, A ;

Sink, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9058-9064

[5] Solid phase synthesis of 1,2-disubstituted alkenes: A novel alkynyldihydropyridine to alkenylpyridine isomerization [J].

Chen, CX ;

Wang, BW ;

Munoz, B .

SYNLETT, 2003, (15) :2404-2406

[6] Use of aromatic radical-anions in the absence of THF.: Tandem formation and cyclization of benzyllithiums derived from the attack of homo- and bishomoallyllithiums on α-methylstyrenes:: Two-pot synthesis of cuparene [J].

Cohen, T ;

Kreethadumrongdat, T ;

Liu, XJ ;

Kulkarni, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3478-3483

[7] SYNTHESIS OF NEW CHIRAL BIS(TRIARYLPHOSPHINE) LIGANDS BASED ON ASYMMETRIC HYDROGENATION OF 4,5-DIARYL-2-OXOCYCLOPENTANECARBOXYLATES [J].

FUKUDA, N ;

MASHIMA, K ;

MATSUMURA, Y ;

TAKAYA, H .

TETRAHEDRON LETTERS, 1990, 31 (49) :7185-7188

[8] MECHANISTIC AND SYNTHETIC STUDIES IN ORGANIC PHOTOCHEMISTRY .12. PHOTODECARBOXYLATION OF ESTERS - PHOTOLYSIS OF ALPHA-NAPHTHALENEMETHYL AND BETA-NAPHTHALENEMETHYL DERIVATIVES [J].

GIVENS, RS ;

MATUSZEW.B ;

NEYWICK, CV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5547-5552

[9] REGIOSELECTIVE ADDITION OF ORGANIC CHLORIDES TO EPOXIDES IN THE PRESENCE OF QUATERNARY AMMONIUM-CHLORIDE [J].

GU, XP ;

IKEDA, I ;

OKAHARA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (01) :397-398

[10] The addition of alkali metals to phenanthrene [J].

Jeanes, A ;

Adams, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :2608-2622

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