A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes

被引：16

作者：

Holmbo, Stephen D. ^{[1
]}

Godfrey, Nicole A. ^{[1
]}

Hirner, Joshua J. ^{[1
,2
]}

Pronin, Sergey V. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

[2] Honeywell UOP, Des Plaines, IL 60016 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 38期

基金：

美国国家科学基金会;

关键词：

ENANTIOSPECIFIC TOTAL-SYNTHESIS; STEREOSPECIFIC TOTAL-SYNTHESIS; ENDO-SELECTIVE CYCLIZATIONS; INDOLE ALKALOIDS; CARBONYL-COMPOUNDS; INTRAMOLECULAR CARBOMERCURATION; ALPHA; BETA-UNSATURATED KETONES; GENERAL-APPROACH; MILD CONDITIONS; VINYL HALIDES;

D O I：

10.1021/jacs.6b06847

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic formal ene reaction between ketone-derived silyl enol ethers and terminal alkynes is described. This transformation is uniquely capable of bimolecular assembly of 2-siloxy-1,4-dienes and can be used to access beta,gamma-unsaturated ketones containing quaternary carbons in the alpha-position

引用

页码：12316 / 12319

页数：4

共 71 条

[1] Synthesis of the C(17)-C(27) fragment of the 20-deoxybryostatins [J].

Almendros, P ;

Rae, A ;

Thomas, EJ .

TETRAHEDRON LETTERS, 2000, 41 (49) :9565-9568

[2] Palladium- and Nickel-Catalyzed Alkenylation of Enolates [J].

Ankner, Tobias ;

Cosner, Casey C. ;

Helquist, Paul .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (06) :1858-1871

[3]

Arisawa M., 2002, SYNTHESIS-STUTTGART, V2002, P138

[4] Synthesis of Fused Carbocycles via a Selective 6-Endo Dig Gold(I)-Catalyzed Carbocyclization [J].

Barabe, Francis ;

Levesque, Patrick ;

Korobkov, Ilia ;

Barriault, Louis .

ORGANIC LETTERS, 2011, 13 (20) :5580-5583

[5] Gold-Catalyzed Synthesis of Carbon-Bridged Medium-Sized Rings [J].

Barabe, Francis ;

Betournay, Genevieve ;

Bellavance, Gabriel ;

Barriault, Louis .

ORGANIC LETTERS, 2009, 11 (18) :4236-4238

[6] Enantioselective Cyclizations of Silyloxyenynes Catalyzed by Cationic Metal Phosphine Complexes [J].

Brazeau, Jean-Francois ;

Zhang, Suyan ;

Colomer, Ignacio ;

Corkey, Britton K. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) :2742-2749

[7]

Brownbridge P., 1983, SYNTHESIS-STUTTGART, V1983, P1

[8] The first enantiospecific synthesis of (-)-koumidine via the intramolecular palladium-catalyzed enolate driven cross coupling reaction.: The stereospecific introduction of the 19-(Z) ethylidene side chain [J].

Cao, H ;

Yu, JM ;

Wearing, XYZ ;

Zhang, CC ;

Liu, XX ;

Deschamps, J ;

Cook, JM .

TETRAHEDRON LETTERS, 2003, 44 (43) :8013-8017

[9] Catalytic asymmetric vinylation of ketone enolates [J].

Chieffi, A ;

Kamikawa, K ;

Åhman, J ;

Fox, JM ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (12) :1897-1900

[10] Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes [J].

Corkey, Britton K. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) :2764-+

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