(Z)-tamoxifen and tetrasubstituted alkenes and dienes via a regio- and stereospecific three-component magnesium carbometalation palladium(0) cross-coupling strategy

被引：71

作者：

Tessier, PE ^{[1
]}

Penwell, AJ ^{[1
]}

Souza, FES ^{[1
]}

Fallis, AG ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ctr Res Biopharmaceut, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 17期

关键词：

D O I：

10.1021/ol0347794

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic The synthesis of various tetrasubstituted alkenes and dienes in a regio- and stereocontrolled manner is described. This three-component coupling strategy involves the addition of Grignard reagents to propargyl alcohols followed by palladium(0)-mediated cross-coupling with aryl or vinyl halides. This protocol has been applied to the synthesis of (Z)-Tamoxifen and related mimics.

引用

页码：2989 / 2992

页数：4

共 26 条

[1] GAMMA-FUNCTIONAL VINYLIC GRIGNARD-REAGENTS .1. REACTIVITY OF ORGANOMAGNESIUM COMPOUNDS WITH ALPHA-ACETYLIC ALCOHOLS IN THE PRESENCE OF CUPROUS HALIDES [J].

DUBOUDIN, JG ;

JOUSSEAUME, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 168 (01) :1-11

[2] GAMMA-FUNCTIONAL VINYL GRIGNARD-REAGENTS .2. IODOLYSIS, ALKYLATION AND ARYLATION OF IODO-ALCOHOLS [J].

DUBOUDIN, JG ;

JOUSSEAUME, B ;

BONAKDAR, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 168 (02) :227-232

[3]

Eisch J. J., 1969, J ORGANOMET CHEM, V20

[4]

EISCH JJ, 1979, J AM CHEM SOC, V101, P1148, DOI 10.1021/ja00499a016

[5] Metal mediated carbometallation of alkynes and alkenes containing adjacent heteroatoms [J].

Fallis, AG ;

Forgione, P .

TETRAHEDRON, 2001, 57 (28) :5899-5913

[6]

Forgione P, 2000, SYNTHESIS-STUTTGART, P921

[7] Magnesium mediated carbometallation of propargyl alcohols: direct routes to furans and furanones [J].

Forgione, P ;

Wilson, PD ;

Fallis, AG .

TETRAHEDRON LETTERS, 2000, 41 (01) :17-20

[8] Magnesium mediated carbometallation of propargyl alcohols: direct routes to dihydroxydienes and enediyne alcohols [J].

Forgione, P ;

Fallis, AG .

TETRAHEDRON LETTERS, 2000, 41 (01) :11-15

[9] THE PHARMACOLOGY AND CLINICAL USES OF TAMOXIFEN [J].

FURR, BJA ;

JORDAN, VC .

PHARMACOLOGY & THERAPEUTICS, 1984, 25 (02) :127-205

[10]

Grese TA, 1996, ANNU REP MED CHEM, V31, P181

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