Domino Asymmetric Conjugate Addition-Conjugate Addition

被引：31

作者：

Germain, Nicolas ^{[1
]}

Schlaefli, Doriane ^{[1
]}

Chellat, Mathieu ^{[1
]}

Rosset, Stephane ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 07期

基金：

瑞士国家科学基金会; 新加坡国家研究基金会;

关键词：

QUATERNARY STEREOGENIC CENTERS; ONE-POT; ENANTIOSELECTIVE SYNTHESIS; TANDEM REACTIONS; ENOL ETHERS; REAGENTS; SULFONES; ALPHA; CONVERSION; FURANS;

D O I：

10.1021/ol5005752

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioenriched Al-, Mg-, and Zn-enolates undergo electrophilic trapping by nitroolefins and vinylsulfones to afford 1,4-diketones and 2-(bis(phenylsulfonyl)ethyl)ketones in good yield and excellent diastereoselectivity. A one-pot preparation of indenes and enantiopure syntheses of tetrahydrobenzofurans, tetrahydrobenzopyrroles, and azulenes are disclosed. A site-selective two-step sequence of three conjugate additions is also demonstrated.

引用

页码：2006 / 2009

页数：4

共 75 条

[51] Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis [J].

Nicolaou, KC ;

Montagnon, T ;

Snyder, SA .

CHEMICAL COMMUNICATIONS, 2003, (05) :551-564

[52]

Paal C., 1884, Ber, V17, P2756, DOI [DOI 10.1002/CBER.188401702228, 10.1002/cber.188401702228]

[53] 2,3-DIHALO-1-(PHENYLSULFONYL)-1-PROPENES AS VERSATILE REAGENTS FOR THE SYNTHESIS OF ANNULATED FURANS AND CYCLOPENTENONES [J].

PADWA, A ;

ISHIDA, M ;

MULLER, CL ;

MURPHREE, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1170-1178

[54] Competitive stereochemical control operative during conrotatory electrocyclization of helically equilibrating diquinanyl-substituted 1,3,5,7-octatetraenyl bisenolates [J].

Paquette, LA ;

Liu, ZS ;

Ramsey, C ;

Gallucci, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (20) :8154-8161

[55] ULTRASOUND IN ORGANIC-SYNTHESIS .7. PREPARATION OF ORGANOZINC REAGENTS AND THEIR NICKEL-CATALYZED REACTIONS WITH ALPHA, BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

PETRIER, C ;

BARBOSA, JCD ;

DUPUY, C ;

LUCHE, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5761-5765

[56]

POSNER GH, 1985, J AM CHEM SOC, V107, P1424, DOI 10.1021/ja00291a060

[57] Highly Enantioselective One-Pot Copper-Catalyzed 1,4 Addition/Organocatalyzed α-Substitution of Enals [J].

Quintard, Adrien ;

Alexakis, Alexandre .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) :1856-1860

[58] From Planning to Optimization: Total Synthesis of Valerenic Acid and Some Bioactive Derivatives [J].

Ramharter, Juergen ;

Mulzer, Johann .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (10) :2041-2053

[59] One-pot asymmetric conjugate addition-trapping of zinc enolates by activated electrophiles [J].

Rathgeb, Xavier ;

March, Sebastien ;

Alexakis, Alexandre .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) :5737-5742

[60] Enantioselective Synthesis of Highly Substituted Furans by a Copper(II)-Catalyzed Cycloisomerization-Indole Addition Reaction [J].

Rauniyar, Vivek ;

Wang, Z. Jane ;

Burks, Heather E. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) :8486-8489

← 1 2 3 4 5 6 7 8 →