Synthesis and diastereoselective complexation of enantiopure sulfinyl dienes: The preparation of sulfinyl iron(0) dienes

被引：58

作者：

Paley, RS ^{[1
]}

deDios, A ^{[1
]}

Estroff, LA ^{[1
]}

Lafontaine, JA ^{[1
]}

Montero, C ^{[1
]}

McCulley, DJ ^{[1
]}

Rubio, MB ^{[1
]}

Ventura, MP ^{[1
]}

Weers, HL ^{[1
]}

delaPradilla, RF ^{[1
]}

Castro, S ^{[1
]}

Dorado, R ^{[1
]}

Morente, M ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,E-28006 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 18期

关键词：

D O I：

10.1021/jo970693a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of a diverse array of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via Stille coupling of halovinyl sulfoxides and vinyl stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of the corresponding sulfinyl diene iron(0) tricarbonyl complexes was accomplished by utilizing Fe(CO)(5)/NMO or (bda)Fe(CO)(3) as iron(0) tricarbonyl transfer reagents. Installation of the iron(0) tricarbonyl fragment was shown to be highly diastereoselective (10-16:1) for (R)-(1Z)-1-sulfinyl dienes, most likely as a result of allylic 1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene is also described.

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页码：6326 / 6343

页数：18

相关论文

共 91 条

[61] STEREOCONTROLLED SYNTHESIS OF ENANTIOMERICALLY PURE DIENYL SULFOXIDES VIA PALLADIUM-CATALYZED COUPLING REACTIONS [J].

PALEY, RS ;

DEDIOS, A ;

DELAPRADILLA, RF .

TETRAHEDRON LETTERS, 1993, 34 (15) :2429-2432

[62]

Patai S., 1988, The Chemistry of Sulphones and Sulphoxides

[63]

Pearson A.J., 1994, IRON COMPOUNDS ORGAN

[64] CHIRAL-AUXILIARY-DIRECTED ASYMMETRIC TRICARBONYLIRON COMPLEXATION OF DIENES [J].

PEARSON, AJ ;

CHANG, K ;

MCCONVILLE, DB ;

YOUNGS, WJ .

ORGANOMETALLICS, 1994, 13 (01) :4-5

[65] OXIDATION OF ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES TO ALKYLSULFINYL SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES [J].

PEREZENCABO, A ;

PERRIO, S ;

SLAWIN, AMZ ;

THOMAS, SE ;

WIERZCHLEYSKI, AT ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :629-642

[66] ASYMMETRIC-SYNTHESIS OF CARBON CARBON BONDS USING SULFINYL CYCLOALKENONES, ALKENOLIDES, AND PYRONES [J].

POSNER, GH .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (02) :72-78

[67] A CONVENIENT PREPARATION OF TRANS-1-CHLOROALKENES (OR CIS)-1-CHLOROALKENES FROM TRANS-1,2-DICHLOROETHYLENE (OR CIS)-1,2-DICHLOROETHYLENE - A NEW SYNTHESIS OF THE SEX-PHEROMONE OF LOBESIA-BOTRANA [J].

RATOVELOMANANA, V ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1981, 22 (04) :315-318

[68] HIGHLY ENANTIOSELECTIVE SYNTHESIS OF A COREY PROSTAGLANDIN INTERMEDIATE [J].

RONAN, B ;

KAGAN, HB .

TETRAHEDRON-ASYMMETRY, 1992, 3 (01) :115-122

[69] ASYMMETRIC ALLYLBORATIONS OF DIENE ALDEHYDE FE(CO)3 DERIVATIVES - EFFICIENT KINETIC RESOLUTION OF RACEMIC COMPLEXES AND THE HIGHLY ENANTIOTOPIC GROUP AND FACE SELECTIVE ALLYLBORATION OF A MESO SUBSTRATE [J].

ROUSH, WR ;

PARK, JC .

TETRAHEDRON LETTERS, 1990, 31 (33) :4707-4710

[70] AN APPROACH TO CHIRAL ETA(4)-BUTADIENE-FE(CO)(3) COMPLEXES VIA DIASTEREOSELECTIVE COMPLEXATION OF NONRACEMIC 2-ALKOXY-4-VINYL-2,5-DIHYDROFURAN DERIVATIVES [J].

SCHMALZ, HG ;

HESSLER, E ;

BATS, JW ;

DURNER, G .

TETRAHEDRON LETTERS, 1994, 35 (26) :4543-4546

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