Ruthenium-catalyzed one-pot carbenoid N-H insertion reactions and diastereoselective synthesis of prolines

被引：99

作者：

Deng, Qing-Hai ^{[1
]}

Xu, Hai-Wei ^{[1
]}

Yuen, Angella Wing-Hoi ^{[2
,3
]}

Xu, Zhen-Jiang ^{[1
]}

Che, Chi-Ming ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China

[2] Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Hom, Hong Kong, Peoples R China

[3] Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Open Lab Chem Biol, Hong Hom, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 08期

关键词：

D O I：

10.1021/ol800087p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl- and aliphatic-substituted 3-hydroxyprolines and various other amino esters are conveniently prepared by [RuCl2(p-cymene)](2)-catalyzed one-pot intramolecular and intermolecular carbenoid N-H insertion reactions, respectively, and the prolines are formed with high diastereoselectivities. The catalytic reactions are tolerant toward air/moisture, and the product yields are insensitive to he organic solvents used.

引用

页码：1529 / 1532

页数：4

共 29 条

[1] THE ROLE OF PROLINE IN THE ASYMMETRIC STEP OF THE WOODWARD SYNTHESIS OF ERYTHROMYCIN
AGAMI, C
PLATZER, N
PUCHOT, C
SEVESTRE, H
[J]. TETRAHEDRON, 1987, 43 (06) : 1091 - 1098
[2] N-H insertion reactions of rhodium carbenoids .1. Preparation of alpha-amino acid and alpha-aminophosphonic acid derivatives
Aller, E
Buck, RT
Drysdale, MJ
Ferris, L
Haigh, D
Moody, CJ
Pearson, ND
Sanghera, JB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24): : 2879 - 2884
[3] Iron corroles and porphyrins as very efficient and highly selective catalysts for the reactions of α-diazo esters with amines
Aviv, I
Gross, Z
[J]. SYNLETT, 2006, (06) : 951 - 953
[4] TOTAL SYNTHESES OF BULGECININE AND BULGECIN-C FROM (2S,4R)-HYDROXYPROLINE
BARRETT, AGM
PILIPAUSKAS, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) : 5194 - 5196
[5] CAMA LD, 1978, TETRAHEDRON LETT, P4233
[6] Rh(II)-catalyzed intramolecular C-H insertion of diazo substrates in water: Scope and limitations
Candeias, Nuno R.
Gois, Pedro M. P.
Afonso, Carlos A. M.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) : 5489 - 5497
[7] Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides
Choi, MKW
Yu, WY
Che, CM
[J]. ORGANIC LETTERS, 2005, 7 (06) : 1081 - 1084
[8] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
Davies, HML
Beckwith, REJ
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2861 - 2903
[9] Catalytic and enantioselective allylic C-H activation with donor-acceptor-substituted carbenoids
Davies, HML
Nikolai, J
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) : 4176 - 4187
[10] Asymmetric synthesis of substituted prolines from δ-amino β-ketoesters.: Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate
Davis, FA
Fang, TN
Goswami, R
[J]. ORGANIC LETTERS, 2002, 4 (09) : 1599 - 1602

← 1 2 3 →