Palladium-catalyzed stereoselective intramolecular cyclization and Suzuki coupling of N-arylsulfonyl-α-chloroenamides promoted by a γ-hydroxy group

被引：4

作者：

Yabuuchi, Yuto ^{[1
]}

Sakamoto, Kenta ^{[1
]}

Yoshimura, Tomoyuki ^{[1
]}

Matsuo, Jun-ichi ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

来源：

TETRAHEDRON | 2018年 / 74卷 / 30期

关键词：

alpha-Chloroenamide; Palladium; Suzuki reaction; Intramolecular cyclization; Hydroxy group; HIGHLY SELECTIVE SYNTHESIS; ALLYLIC ALCOHOLS; CONVENIENT SYNTHESIS; ARYLATION; ENAMIDES; YNAMIDES; REGIO; HYDROHALOGENATION; ALKENYLATION;

D O I：

10.1016/j.tet.2018.06.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Suzuki reaction of both (E)- and (Z)-alpha-chloro-gamma-hydroxyenamides with benzeneboronic acid by using Pd-2(dba)(3), tBu(3)P, and Cs2CO3 proceeded stereoselectively to afford only (E)-trisubstituted enamides. Also, palladium-catalyzed intramolecular cyclization of (E)- and (Z)-alpha-chloro-gamma-hydroxyenamides bearing an N-arylsulfonyl group took place stereoselectively to give the corresponding (E)-2,3-dihydrobenzoisothiazole 1,1-dioxides. The gamma-hyroxy group in alpha-chloroenamides was found to accelerate the present palladium-catalyzed carbon-carbon bond forming reactions. (C) 2018 Elsevier Ltd. All rights reserved.

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页码：4053 / 4061

页数：9

相关论文

共 29 条

[1] PALLADIUM-CATALYZED VINYLATION OF ALLYLIC ALCOHOLS WITH ENOL TRIFLATES - A CONVENIENT SYNTHESIS OF CONJUGATED DIENOLS [J].

BERNOCCHI, E ;

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1992, 33 (21) :3073-3076

[2] Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides [J].

Compain, Guillaume ;

Jouvin, Kevin ;

Martin-Mingot, Agnes ;

Evano, Gwilherm ;

Marrot, Jerome ;

Thibaudeau, Sebastien .

CHEMICAL COMMUNICATIONS, 2012, 48 (42) :5196-5198

[3] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[4] Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides:: Application to the synthesis of disubstituted ynamides [J].

Couty, S ;

Barbazanges, M ;

Meyer, C ;

Cossy, J .

SYNLETT, 2005, (06) :905-910

[5] Regio- and stereoselective hydrohalogenation of ynamide components in 1,3-butadiynes with in situ generated HX [J].

Ide, Masataka ;

Ohashi, Kazuhiro ;

Mihara, Shigenori ;

Iwasawa, Tetsuo .

TETRAHEDRON LETTERS, 2014, 55 (13) :2130-2133

[6] PALLADIUM-CATALYZED REACTION OF VINYLIC HALIDES WITH ALLYLIC ALCOHOLS - A HIGHLY CHEMOCONTROLLED, REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF CONJUGATED DIENOLS [J].

JEFFERY, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) :324-325

[7] PALLADIUM-CATALYZED ARYLATION OF ALLYLIC ALCOHOLS - HIGHLY SELECTIVE SYNTHESIS OF BETA-AROMATIC CARBONYL-COMPOUNDS OR BETA-AROMATIC ALPHA,BETA-UNSATURATED ALCOHOLS [J].

JEFFERY, T .

TETRAHEDRON LETTERS, 1991, 32 (19) :2121-2124

[8] Diastereotopic Group Selection in Hydroxy-Directed Intramolecular C-H Alkenylation of Indole under Oxidative Palladium(II) Catalysis [J].

Kandukuri, Sandeep R. ;

Jiao, Lin-Yu ;

Machotta, Axel B. ;

Oestreich, Martin .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1597-1609

[9] PALLADIUM-CATALYZED ARYLATION OF ALLYLIC DIOLS - HIGHLY SELECTIVE SYNTHESIS OF PHENYL-SUBSTITUTED ALLYLIC DIOLS [J].

KANG, SK ;

JUNG, KY ;

PARK, CH ;

NAMKOONG, EY ;

KIM, TH .

TETRAHEDRON LETTERS, 1995, 36 (35) :6287-6290

[10] Complete regioselection in palladium-catalyzed arylation and alkenylation of allylic alcohols with hypervalent iodonium salts [J].

Kang, SK ;

Lee, HW ;

Jang, SB ;

Kim, TH ;

Pyun, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2604-2605