Palladium-catalyzed intramolecular α-arylation of α-amino acid esters

被引：122

作者：

Gaertzen, O ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 02期

关键词：

D O I：

10.1021/jo0107756

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd-catalyzed intramolecular alpha-arylation of alpha-amino acid esters is described. Starting from readily available amino acids, the synthesis of a variety of isoindolines and tetrahydroisoquinoline carboxylic acid esters has been accomplished. Additionally, fused tricyclic systems can be efficiently prepared from cyclic amino acid esters. Reaction conditions have been found that allow the use of tert-butyl ester and N-(benzyloxycarbonyl) protecting groups.

引用

页码：465 / 475

页数：11

共 79 条

[1] Asymmetric arylation of ketone enolates
Ahman, J
Wolfe, JP
Troutman, MV
Palucki, M
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) : 1918 - 1919
[2] Suggested modifications to a distillation-free solvent purification system
Alaimo, PJ
Peters, DW
Arnold, J
Bergman, RG
[J]. JOURNAL OF CHEMICAL EDUCATION, 2001, 78 (01) : 64 - 64
[3] Identification of the effective palladium(0) catalytic species generated in situ from mixtures of Pd(dba)(2) and bidentate phosphine ligands. Determination of their rates and mechanism in oxidative addition
Amatore, C
Broeker, G
Jutand, A
Khalil, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (22) : 5176 - 5185
[4] Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides
Beller, M
Breindl, C
Riermeier, TH
Tillack, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) : 1403 - 1412
[5] Novel multidrug resistance reversal agents
Berger, D
Citarella, R
Dutia, M
Greenberger, L
Hallett, W
Paul, R
Powell, D
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (12) : 2145 - 2161
[6] BIOXALOMYCINS, NEW ANTIBIOTICS PRODUCED BY THE MARINE STREPTOMYCES SP LL-31F508 - TAXONOMY AND FERMENTATION
BERNAN, VS
MONTENEGRO, DA
KORSHALLA, JD
MAIESE, WM
STEINBERG, DA
GREENSTEIN, M
[J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (12) : 1417 - 1424
[7] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
BLANCHETTE, MA
CHOY, W
DAVIS, JT
ESSENFELD, AP
MASAMUNE, S
ROUSH, WR
SAKAI, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
[8] Brunner H, 2000, EUR J ORG CHEM, V2000, P2119
[9] PALLADIUM-CATALYZED COUPLING REACTIONS OF ARYL TRIFLATES OR HALIDES WITH KETENE TRIMETHYLSILYL ACETALS - A NEW ROUTE TO ALKYL 2-ARYLALKANOATES
CARFAGNA, C
MUSCO, A
SALLESE, G
SANTI, R
FIORANI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 261 - 263
[10] REACTIONS OF (ARENE)TRICARBONYLCHROMIUM COMPLEXES WITH ANIONS FROM SCHIFF-BASES OF ALPHA-AMINO ESTERS - SYNTHESIS OF ALPHA-ARYL AMINO-ACIDS
CHAARI, M
LAVERGNE, JP
VIALLEFONT, P
[J]. SYNTHETIC COMMUNICATIONS, 1989, 19 (7-8) : 1211 - 1216

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