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
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
收藏
页码:7393 / 7397
页数:5
相关论文
共 36 条
[21]   Palladium-catalyzed annulation of allenes using functionally substituted vinylic halides [J].
Larock, RC ;
He, Y ;
Leong, WW ;
Han, X ;
Refvik, MD ;
Zenner, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2154-2160
[22]   PALLADIUM(II)-MEDIATED ROUTES TO FUNCTIONALIZED HETEROCYCLES [J].
LATHBURY, D ;
VERNON, P ;
GALLAGHER, T .
TETRAHEDRON LETTERS, 1986, 27 (49) :6009-6012
[23]   ASYMMETRIC-SYNTHESIS VIA ALLENES - SYNTHESIS OF (R)-(-)-CONIINE [J].
LATHBURY, D ;
GALLAGHER, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (02) :114-115
[24]   Chiral allylic and allenic stannanes as reagents for asymmetric synthesis [J].
Marshall, JA .
CHEMICAL REVIEWS, 1996, 96 (01) :31-47
[25]   A new method for the synthesis of nitrogen heterocycles via palladium catalyzed intramolecular hydroamination of allenes [J].
Meguro, M ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 1998, 39 (30) :5421-5424
[26]  
MEGURO M, 1995, TETRAHEDRON LETT, V60, P3764
[27]   Metal-initiated amination of alkenes and alkynes [J].
Muller, TE ;
Beller, M .
CHEMICAL REVIEWS, 1998, 98 (02) :675-703
[28]   UNSATURATED ESTER SYNTHESIS VIA CU(I)-CATALYZED ALLYLATION OF ZINC ESTERS [J].
OCHIAI, H ;
TAMARU, Y ;
TSUBAKI, K ;
YOSHIDA, Z .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4418-4420
[29]   First palladium-catalyzed aziridination reaction of amino allenes [J].
Ohno, H ;
Toda, A ;
Miwa, Y ;
Taga, T ;
Osawa, E ;
Yamaoka, Y ;
Fujii, N ;
Ibuka, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :2992-2993
[30]  
PRASAD JS, 1988, TETRAHEDRON LETT, V29, P4257