Cp*Ir complex-catalyzed N-heterocyclization of primary amines with diols:: A new catalytic system for environmentally benign synthesis of cyclic amines

被引:244
作者
Fujita, KI [1 ]
Fujii, T [1 ]
Yamaguchi, R [1 ]
机构
[1] Kyoto Univ, Grad Sch Human & Environm Studies, Kyoto 6068501, Japan
关键词
D O I
10.1021/ol048619j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new efficient method for the N-heterocyclization of primary amines with diols catalyzed by a Cp*Ir complex was developed. A variety of five-, six-, and seven-membered cyclic amines were synthesized in good to excellent yields with the formation of only water as a byproduct. A two-step asymmetric synthesis of (S)-2-phenylpiperidine was also achieved using (R)-1-phenylethylamine as a starting primary amine.
引用
收藏
页码:3525 / 3528
页数:4
相关论文
共 30 条
[1]   Ruthenium-complex-catalyzed N-(cyclo)alkylation of aromatic amines with diols.: Selective synthesis of N-(ω-hydroxyalkyl)anilines of type PhNH(CH2)nOH and of some bioactive arylpiperazines [J].
Abbenhuis, RATM ;
Boersma, J ;
van Koten, G .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4282-4290
[2]   Enantioselective synthesis of 2-arylpiperidines from chiral lactams.: A concise synthesis of (-)-anabasine [J].
Amat, M ;
Cantó, M ;
Llor, N ;
Bosch, J .
CHEMICAL COMMUNICATIONS, 2002, (05) :526-527
[3]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[4]   SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES, OXANES, AND THIANES [J].
BALIAH, V ;
JEYARAMAN, R ;
CHANDRASEKARAN, L .
CHEMICAL REVIEWS, 1983, 83 (04) :379-423
[5]  
Bird C. W., 1996, COMPREHENSIVE HETERO
[6]   Synthesis of heterocycles by radical cyclisation [J].
Bowman, WR ;
Fletcher, AJ ;
Potts, GBS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2747-2762
[7]  
CORWIN AH, 1950, HETEROCYCL COMPOUNDS, V1, P277
[8]   Synthesis and applications of nonracemic β-amino aldehydes to the asymmetric synthesis of piperdines:: (+)-dihydropinidine [J].
Davis, FA ;
Szewczyk, JM .
TETRAHEDRON LETTERS, 1998, 39 (33) :5951-5954
[9]   δ-amino β-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis.: Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A [J].
Davis, FA ;
Chao, B ;
Fang, TN ;
Szewczyk, JM .
ORGANIC LETTERS, 2000, 2 (08) :1041-1043
[10]   TRANSFORMATION OF ORGANIC-COMPOUNDS IN THE PRESENCE OF METAL-COMPLEXES .5. CYCLIZATION OF AMINOALCOHOLS ON A RUTHENIUM COMPLEX [J].
FELFOLDI, K ;
KLYAVLIN, MS ;
BARTOK, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 362 (1-2) :193-195