Palladium-catalyzed regio- and stereoselective synthesis of N-protected 2,4-dialkylated azacyclobutanes from amino allenes

被引：40

作者：

Anzai, M ^{[1
]}

Toda, A ^{[1
]}

Ohno, H ^{[1
]}

Takemoto, Y ^{[1
]}

Fujii, N ^{[1
]}

Ibuka, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(99)01517-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed reaction of N-arylsulfonyl-1-alkyl-3,4-dienylamines with an aryl iodide in the presence of potassium carbonate in DMF at around 70 degrees C affords most predominantly the 2,4-cis-disubstituted azacyclobutanes bearing an aryl group on the double bond in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7393 / 7397

页数：5

共 36 条

[1] The two component palladium catalyst system for intermolecular hydroamination of allenes [J].

AlMasum, M ;

Meguro, M ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 1997, 38 (34) :6071-6074

[2] Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoallenes [J].

Arredondo, VM ;

McDonald, FE ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4871-4872

[3] CYCLIZATION OF GAMMA-ALLENIC AND DELTA-ALLENIC AMINES - SYNTHESIS OF 2-ALCENYL PYRROLIDINES AND 2-ALCENYL PIPERIDENES [J].

ARSENIYADIS, S ;

GORE, J .

TETRAHEDRON LETTERS, 1983, 24 (37) :3997-4000

[4] AN EFFICIENT SYNTHESIS OF (+/-)-PINIDINE [J].

ARSENIYADIS, S ;

SARTORETTI, J .

TETRAHEDRON LETTERS, 1985, 26 (06) :729-732

[5] SYNTHESIS OF ALLYLIC AMINES THROUGH THE PALLADIUM-CATALYZED HYDROAMINATION OF ALLENES [J].

BESSON, L ;

GORE, J ;

GAZES, B .

TETRAHEDRON LETTERS, 1995, 36 (22) :3857-3860

[6] ALLENES AND ACETYLENES .18. SYNTHESIS OF 3-PYRROLINES BY SILVER(I)-CATALYZED CYCLIZATION OF ALLENIC AMINES [J].

CLAESSON, A ;

SAHLBERG, C ;

LUTHMAN, K .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (04) :309-310

[7]

DAVIES IW, 1993, SYNLETT, P85

[8] SYNTHESIS OF ENANTIOMERICALLY PURE UNSATURATED ALPHA-AMINO-ACIDS USING SERINE-DERIVED ZINZ/COPPER REAGENTS [J].

DUNN, MJ ;

JACKSON, RFW ;

PIETRUSZKA, J ;

TURNER, D .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2210-2215

[9] ENANTIOSELECTIVE SYNTHESIS OF PUMILIOTOXIN-251D - A STRATEGY EMPLOYING AN ALLENE-BASED ELECTROPHILE-MEDIATED CYCLIZATION [J].

FOX, DNA ;

LATHBURY, D ;

MAHON, MF ;

MOLLOY, KC ;

GALLAGHER, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2652-2656

[10] ASYMMETRIC-SYNTHESIS OF FUNCTIONALIZED PYRROLIDINES - THE ROLE OF A STEREOGENIC CENTER ON NITROGEN [J].

FOX, DNA ;

LATHBURY, D ;

MAHON, MF ;

MOLLOY, KC ;

GALLAGHER, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (15) :1073-1075

← 1 2 3 4 →