New and efficient synthesis of azabicyclo[4.4.0]alkane amino acids by Rh-catalyzed cyclohydrocarbonylation

被引:29
作者
Mizutani, N [1 ]
Chiou, WH [1 ]
Ojima, I [1 ]
机构
[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA
关键词
D O I
10.1021/ol026782d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly efficient syntheses of azabicyclo[4.4.0]alkane amino acids were achieved by Rh-catalyzed cyclohydrocarbonylation of dipeptides bearing a terminal olefin moiety and a heteroatom nucleophile.
引用
收藏
页码:4575 / 4578
页数:4
相关论文
共 14 条
[1]   Design, synthesis, and dopamine receptor modulating activity of diketopiperazine peptidomimetics of L-prolyl-L-leucylglycinamide [J].
Baures, PW ;
Ojala, WH ;
Costain, WJ ;
Ott, MC ;
Pradhan, A ;
Gleason, WB ;
Mishra, RK ;
Johnson, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) :3594-3600
[2]   THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .61. THE PREPARATION OF QUINAZOLINES AND QUINAZOLINONES INVOLVING RHODIUM-CATALYZED HYDROFORMYLATION OF ALKENYL ANILINES [J].
CAMPI, EM ;
JACKSON, WR ;
MCCUBBIN, QJ ;
TRNACEK, AE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (06) :1061-1070
[3]   Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics [J].
Colombo, L ;
Di Giacomo, M ;
Brusotti, G ;
Sardone, N ;
Angiolini, M ;
Belvisi, L ;
Maffioli, S ;
Manzoni, L ;
Scolastico, C .
TETRAHEDRON, 1998, 54 (20) :5325-5336
[4]   Rigid dipeptide surrogates: Syntheses of enantiopure quinolizidinone and pyrroloazepinone amino acids from a common diaminodicarboxylate precursor [J].
Gosselin, F ;
Lubell, WD .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2163-2171
[5]   Short synthesis of (3S,6S,9S)-2-oxo-3-(N-Boc-amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid methyl ester: Tandem cyclization protocol [J].
Kim, HO ;
Kahn, M .
TETRAHEDRON LETTERS, 1997, 38 (37) :6483-6484
[6]   Malic acid: A convenient precursor for the synthesis of peptide secondary structure mimetics [J].
Kim, HO ;
Lum, C ;
Lee, MS .
TETRAHEDRON LETTERS, 1997, 38 (28) :4935-4938
[7]   SYNTHESIS OF ENANTIOPURE ALPHA,OMEGA-DIAMINO DICARBOXYLATES AND AZABICYCLOALKANE AMINO-ACIDS BY CLAISEN CONDENSATION OF ALPHA-[N-(PHENYLFLUORENYL)AMINO] DICARBOXYLATES [J].
LOMBART, HG ;
LUBELL, WD .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6147-6149
[8]   Rigid dipeptide mimetics: Efficient synthesis of enantiopure indolizidinone amino acids [J].
Lombart, HG ;
Lubell, WD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9437-9446
[9]   NEW AND EFFICIENT ROUTE TO PIPECOLIC ACID-DERIVATIVES BY MEANS OF RH-CATALYZED INTRAMOLECULAR CYCLOHYDROCARBONYLATION [J].
OJIMA, I ;
TZAMARIOUDAKI, M ;
EGUCHI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7078-7079
[10]  
OTSUKA M, 1985, CHEM PHARM BULL, V33, P509