Further observations on the rhodium (I)-catalysed tandem hydrosilylation-intramolecular aldol reaction

被引：43

作者：

Freiría, M

Whitehead, AJ

Tocher, DA

Motherwell, WB

机构：

[1] UCL, Dept Chem, Christopher Ingold Labs, London WC1H 0AJ, England

[2] GlaxoSmithKline Res & Dev Ltd, Chem Dev Div, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON | 2004年 / 60卷 / 11期

关键词：

tandem hydrosilylation; aldol; rhodium; intramolecular; catalytic;

D O I：

10.1016/j.tet.2003.12.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rhodium (1) catalysed tandem hydrosilylation-intramolecular aldol reaction provides a simple strategy for construction of a range of usefully functionalised five-membered rings from readily prepared 6-oxo-2-hexenoates in good yield and with good to excellent stereoselectivity. A series of silanes and rhodium catalysts have been investigated. Stereoselectivity proved to be highly dependant on the catalyst as well as on the substitution pattern of the parent substrate. The extension of this methodology for the synthesis of larger ring sizes has also been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2673 / 2692

页数：20

相关论文

共 86 条

[71] ASYMMETRIC CYCLIZATION REACTIONS BY RH(I) WITH CHIRAL LIGANDS [J].

TAURA, Y ;

TANAKA, M ;

FUNAKOSHI, K ;

SAKAI, K .

TETRAHEDRON LETTERS, 1989, 30 (46) :6349-6352

[72] Catalytic diastereoselective reductive aldol reaction: Optimization of interdependent reaction variables by arrayed catalyst evaluation [J].

Taylor, SJ ;

Morken, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12202-12203

[73] Rhodium-catalyzed enantioselective reductive aldol reaction [J].

Taylor, SJ ;

Duffey, MO ;

Morken, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4528-4529

[74] SEQUENTIAL TRANSFORMATIONS IN ORGANIC-CHEMISTRY - A SYNTHETIC STRATEGY WITH A FUTURE [J].

TIETZE, LF ;

BEIFUSS, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (02) :131-163

[75] Conjugate addition to (α,β)(α′,β′)-diendioate esters by lithium (α-methylbenzyl)benzylamide:: tandem addition-cyclisation versus double addition [J].

Urones, JG ;

Garrido, NM ;

Díez, D ;

Dominguez, SH ;

Davies, SG .

TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1637-1641

[76] NEW TYPE OF CYCLIZATION OF ALPHA,BETA,CHI,PSI-UNSATURATED DIOIC ACID-ESTERS THROUGH TANDEM CONJUGATE ADDITIONS BY USING LITHIUM N-BENZYL-N-(TRIMETHYLSILYL)AMIDE AS A NITROGEN NUCLEOPHILE [J].

UYEHARA, T ;

SHIDA, N ;

YAMAMOTO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :3139-3145

[77] Organocatalytic Michael cycloisomerization of bis(enones): The intramolecular Rauhut-Currier reaction [J].

Wang, LC ;

Luis, AL ;

Agaplou, K ;

Jang, HY ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2402-2403

[78]

WHITEHEAD AJ, 1995, THESIS U E ANGLIA

[79] NOVEL PHOTOCHEMICAL REARRANGEMENTS OF CITRAL AND RELATED-COMPOUNDS AT ELEVATED-TEMPERATURES [J].

WOLFF, S ;

BARANY, F ;

AGOSTA, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (07) :2378-2386

[80] HIGHLY DIASTEREOSELECTIVE, ENANTIOSELECTIVE CYCLIZATION OF SYMMETRICAL 3,4-DISUBSTITUTED 4-PENTENAL USING CHIRAL RHODIUM(I)-COMPLEX [J].

WU, XM ;

FUNAKOSHI, K ;

SAKAI, K .

TETRAHEDRON LETTERS, 1993, 34 (37) :5927-5930

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