Regioselectivity Switch: Gold(I)-Catalyzed Oxidative Rearrangement of Propargyl Alcohols to 1,3-Diketones

被引：126

作者：

Hashmi, A. Stephen K. ^{[1
]}

Wang, Tao ^{[1
]}

Shi, Shuai ^{[1
]}

Rudolph, Matthias ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 17期

关键词：

CATALYZED RING EXPANSION; ONE-POT SYNTHESIS; GOLD CATALYSIS; BETA-DIKETONES; CYCLIZATION; KETONES; ROUTE;

D O I：

10.1021/jo301381z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The gold(I)-catalyzed oxidative rearrangement of propargyl alcohols provides an efficient and selective route to 1,3-diketones under mild conditions. Pyridine-N-oxides were used as external oxidants with, different from related substrates, no alkylidenecycloalkanones or oxetan-3-ones formed as side-products.

引用

页码：7761 / 7767

页数：7

共 50 条

[1] Ring Enlargement versus Selenoetherification on the Reaction of Allenyl Oxindoles with Selenenylating Reagents [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo ;

Gomez-Campillos, Gonzalo ;

Rosario Torres, M. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) :3549-3556

[2] Gold catalyzed oxycyclizations of alkynols and alkyndiols [J].

Alcaide, Benito ;

Almendros, Pedro ;

Miguel Alonso, Jose .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) :4405-4416

[3]

[Anonymous], 1980, British Patent, Patent No. [GB 1568855, 1568855]

[4] High-Yielding Oxidation of β-Hydroxyketones to β-Diketones Using o-Iodoxybenzoic Acid [J].

Bartlett, Samuel L. ;

Beaudry, Christopher M. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9852-9855

[5] BETA-DIKETONES .4. SYNTHESIS OF MONOSUBSTITUTED BENZOYLCYCLOPENTANONES [J].

CAMPBELL, RD ;

HARMER, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :379-&

[6] Gold- and Iodine-Mediated Internal Oxygen Transfer of Nitrone- and Sulfoxide-Functionalized Alkynes [J].

Chen, Dan ;

Song, Guoyong ;

Jia, Aiqun ;

Li, Xingwei .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20) :8488-8494

[7]

CIRIGOTTIS KA, 1974, AUST J CHEM, V27, P234

[8] Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes [J].

Cuenca, Ana B. ;

Montserrat, Sergi ;

Hossain, Kabir M. ;

Mancha, Gisela ;

Lledos, Agusti ;

Medio-Simon, Mercedes ;

Ujaque, Gregori ;

Asensio, Gregorio .

ORGANIC LETTERS, 2009, 11 (21) :4906-4909

[9] Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[b]azepin-4-ones from Tertiary N-(But-3-ynyl)anilines [J].

Cui, Li ;

Zhang, Guozhu ;

Peng, Yu ;

Zhang, Liming .

ORGANIC LETTERS, 2009, 11 (06) :1225-1228

[10] Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Martin, Nicolas .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :379-381

← 1 2 3 4 5 →