Rh(I)-Catalyzed Asymmetric Synthesis of 3-Substituted Isoindolinones through CO Gas-Free Aminocarbonylation

被引：51

作者：

Fujioka, Masahiko ^{[1
]}

Morimoto, Tsumoru ^{[1
]}

Tsumagari, Takayuki ^{[1
]}

Tanimoto, Hiroki ^{[1
]}

Nishiyama, Yasuhiro ^{[1
]}

Kakiuchi, Kiyomi ^{[1
]}

机构：

[1] Nara Inst Sci & Technol NAIST, Grad Sch Mat Sci, Nara 6300192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 06期

关键词：

FREE CARBONYLATIVE CYCLIZATION; CHIRAL DIENE LIGANDS; RHODIUM-CATALYZED ARYLATION; DIELS-ALDER REACTIONS; N-TOSYLARYLIMINES; HYDROFORMYLATION; FORMALDEHYDE; OLEFINS; EFFICIENT; ISOINDOLIN-1-ONES;

D O I：

10.1021/jo300201g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and accessible synthesis of chiral 3-substituted isoindolinone frameworks is described. The synthesis involved the Rh(I)catalyzed asymmetric arylation of boronic acids to 2-halobenzaldimines and the subsequent Rh(I)-catalyzed intramolecular aminocarbonylation of the resulting 2-halobenzylamines using an aldehyde as the carbonyl source. The method tolerates a variety of functional groups, yielding isoindolinone derivatives in moderate to high yields with high ee-values. In addition, two Rh(I)-catalyzed transformations could be efficiently accomplished in a one-pot sequence to give chiral isoindolinones by the simple addition of a ligand and an aldehyde after the Rh(I)-catalyzed asymmetric arylation.

引用

页码：2911 / 2923

页数：13

共 83 条

[1] Hydroformylation of olefins with formaldehyde in the presence of RhHCO(PPh3)3 [J].

Ahn, HS ;

Han, SH ;

Uhm, SJ ;

Seok, WK ;

Lee, HN ;

Korneeva, GA .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 144 (02) :295-306

[2] The aza-[2,3]-Wittig sigmatropic rearrangement of acyclic amines: Scope and limitations of silicon assistance [J].

Anderson, JC ;

Flaherty, A ;

Swarbrick, ME .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9152-9156

[3] The benzodiazepine binding site of GABAA receptors as a target for the development of novel anxiolytics [J].

Atack, JR .

EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2005, 14 (05) :601-618

[4] Absolute configuration of sporotricale and structure of 6-hydroxysporotricale [J].

Bava, Adriana ;

Dallavalle, Sabrina ;

Fronza, Giovanni ;

Nasini, Gianluca ;

de Pava, Orso Vajna .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (12) :1793-1795

[5] Isoindolinone enantiomers having affinity for the dopamine D4 receptor [J].

Belliotti, TR ;

Brink, WA ;

Kesten, SR ;

Rubin, JR ;

Wustrow, DJ ;

Zoski, KT ;

Whetzel, SZ ;

Corbin, AE ;

Pugsley, TA ;

Heffner, TG ;

Wise, LD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) :1499-1502

[6] Discovery of novel, orally active dual NK1/NK2 antagonists [J].

Bernstein, PR ;

Aharony, D ;

Albert, JS ;

Andisik, D ;

Barthlow, HG ;

Bialecki, R ;

Davenport, T ;

Dedinas, RF ;

Dembofsky, BT ;

Koether, G ;

Kosmider, BJ ;

Kirkland, K ;

Ohnmacht, CJ ;

Potts, W ;

Rumsey, WL ;

Shen, LH ;

Shenvi, A ;

Sherwood, S ;

Stollman, D ;

Russell, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (20) :2769-2773

[7] A new and efficient palladium-catalyzed synthesis of a 2,3,4,5-tetrahydro-1H-2,4-benzodiazepine-1,3-dione derivative [J].

Bocelli, G ;

Catellani, M ;

Cugini, F ;

Ferraccioli, R .

TETRAHEDRON LETTERS, 1999, 40 (13) :2623-2624

[8] Syntheses of Substituted 3-Methyleneisoindolin-1-ones By a Palladium-Catalyzed Sonogashira Coupling-Carbonylation-Hydroamination Sequence in Phosphonium Salt-Based Ionic liquids [J].

Cao, Hong ;

McNamee, Laura ;

Alper, Howard .

ORGANIC LETTERS, 2008, 10 (22) :5281-5284

[9] Human cytochrome P450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components [J].

Chatterjee, P ;

Franklin, MR .

DRUG METABOLISM AND DISPOSITION, 2003, 31 (11) :1391-1397

[10] Studies on the diastereoselective reductive alkylation of (R)-phenylglycinol derived phthalimide:: observation of stereoelectronic effects [J].

Chen, MD ;

He, MZ ;

Zhou, X ;

Huang, LQ ;

Ruan, YP ;

Huang, PQ .

TETRAHEDRON, 2005, 61 (05) :1335-1344

← 1 2 3 4 5 6 7 8 9 →