Selective azetidine and tetrahydropyridine formation via Pd-catalyzed cyclizations of allene-substituted amines and amino acids

被引:74
作者
Rutjes, FPJT
Tjen, KCMF
Wolf, LB
Karstens, WFJ
Schoemaker, HE
Hiemstra, H
机构
[1] Univ Amsterdam, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands
[2] DSM Res, Dept Organ Chem & Biotechnol, NL-6160 MD Geleen, Netherlands
关键词
D O I
10.1021/ol990700c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] By choosing the right substituents either highly functionalized unusual four-membered ring amino acids or the isomeric pipecolic acid derivatives are obtained in enantiomerically pure form. Starting material is a linear allene containing amino acid that has been resolved via biocatalysis.
引用
收藏
页码:717 / 720
页数:4
相关论文
共 41 条
[1]   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
[2]   ACETYLENES .3. REACTIONS WITH LITHIUM ALUMINUM HYDRIDE [J].
BAILEY, WJ ;
PFEIFER, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (10) :1337-1341
[3]   ALLENE TRANSFER-REACTIONS - A NEW SYNTHESIS OF TERMINAL ALLENES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BASAK, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1284-1285
[4]   PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 2,3-BUTADIANYLMALONATES TO GAMMA-LACTONES [J].
BESSON, L ;
BAZIN, J ;
GORE, J ;
CAZES, B .
TETRAHEDRON LETTERS, 1994, 35 (18) :2881-2884
[5]   ALLENES .17. SYNTHESIS OF ALLENIC CYANOHYDRINS AMINONITRILES AND AMINO-ACIDS FROM ALLENIC ALDEHYDES [J].
BLACK, DK ;
LANDOR, SR .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (03) :281-&
[6]   ALLENES .18. SYNTHESIS OF ALLENIC AMINO-ACIDS FROM ALLENIC BROMIDES AND DIETHYL FORMYLAMINOMALONATE [J].
BLACK, DK ;
LANDOR, SR .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (03) :283-&
[7]  
BOESTEN WHJ, 1987, Patent No. 4705752
[8]  
CAZES B, 1988, SYNTHESIS-STUTTGART, P983
[9]  
CHILTON WS, 1968, TETRAHEDRON LETT, P6283
[10]  
DAVIES IW, 1993, SYNLETT, P85