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

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 26期

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

页码：4575 / 4578

页数：4

共 14 条

[1] Design, synthesis, and dopamine receptor modulating activity of diketopiperazine peptidomimetics of L-prolyl-L-leucylglycinamide
Baures, PW
Ojala, WH
Costain, WJ
Ott, MC
Pradhan, A
Gleason, WB
Mishra, RK
Johnson, RL
[J]. 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
CAMPI, EM
JACKSON, WR
MCCUBBIN, QJ
TRNACEK, AE
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (06) : 1061 - 1070
[3] Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics
Colombo, L
Di Giacomo, M
Brusotti, G
Sardone, N
Angiolini, M
Belvisi, L
Maffioli, S
Manzoni, L
Scolastico, C
[J]. TETRAHEDRON, 1998, 54 (20) : 5325 - 5336
[4] Rigid dipeptide surrogates: Syntheses of enantiopure quinolizidinone and pyrroloazepinone amino acids from a common diaminodicarboxylate precursor
Gosselin, F
Lubell, WD
[J]. 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
Kim, HO
Kahn, M
[J]. TETRAHEDRON LETTERS, 1997, 38 (37) : 6483 - 6484
[6] Malic acid: A convenient precursor for the synthesis of peptide secondary structure mimetics
Kim, HO
Lum, C
Lee, MS
[J]. 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
LOMBART, HG
LUBELL, WD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6147 - 6149
[8] Rigid dipeptide mimetics: Efficient synthesis of enantiopure indolizidinone amino acids
Lombart, HG
Lubell, WD
[J]. 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
OJIMA, I
TZAMARIOUDAKI, M
EGUCHI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) : 7078 - 7079
[10] OTSUKA M, 1985, CHEM PHARM BULL, V33, P509

← 1 2 →