A straightforward approach towards piperidines via Stille coupling and subsequent 1,4-addition of amines

被引：19

作者：

Dörrenbächer, S

Kazmaier, U ^{[1
]}

Ruf, S

机构：

[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany

[2] Sanofi Aventis, Chem Sci, D-65926 Frankfurt, Germany

来源：

SYNLETT | 2006年 / 04期

关键词：

heterocycles; hydrostannations; piperidines; Stille couplings;

D O I：

10.1055/s-2006-926246

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted 4-piperidones are easily obtained from alkynes via molybdenum-catalyzed regioselective hydrostannation and subsequent Stille-coupling of the vinyl stannanes obtained with alpha.beta-unsaturated acyl chlorides. The resulting divinylketones can undergo a double 1,4-addition of amines giving rise to the required 4-piperidones. The best results are obtained if the Stille couplings and the 1.4-additions are combined in a one-pot procedure.

引用

页码：547 / 550

页数：4

共 37 条

[1] ALBRECHT M, 2003, ANGEW CHEM INT EDIT, V40, P3750
[2] Albrecht M., 2001, ANGEW CHEM, V113, P3866, DOI DOI 10.1002/1521-3773(20011015)113:20<3866::AID-ANGE3866>3.0.C0
[3] 2-Y
[4] [Anonymous], 1994, ANGEW CHEM, V106, P1858
[5] Barco A, 2001, EUR J ORG CHEM, V2001, P975
[6] BLASKO G, 1987, ARZNEIMITTEL-FORSCH, V37-1, P667
[7] Molybdenum-catalyzed stannylations as key steps in heterocyclic synthesis
Braune, S
Pohlman, M
Kazmaier, U
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (02) : 468 - 474
[8] Regioselective hydrostannations catalyzed by molybdenum isonitrile complexes
Braune, S
Kazmaier, U
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 641 (1-2) : 26 - 29
[9] Davies A.G., 2004, Organotin Chemistry, V2nd, DOI 10.1002/3527601899.ch13
[10] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS
FARINA, V
KRISHNAN, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9585 - 9595

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