Diastereoselective allylations of enantiopure 3- and 4-substituted η4-(1Z)-(sulfinyldienal)iron(0) tricarbonyl complexes

被引：12

作者：

Paley, RS ^{[1
]}

Estroff, LA

McCulley, DJ

Martinez-Cruz, LA

Sanchez, AJ

Cano, FH

机构：

[1] Swarthmore Coll, Dept Chem, Swarthmore, PA 19081 USA

[2] CSIC, Inst Quim Fis Rocasolano, Dept Cristalog, E-28006 Madrid, Spain

来源：

ORGANOMETALLICS | 1998年 / 17卷 / 09期

关键词：

D O I：

10.1021/om970615d

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diastereoselectivity of allylations of enantiopure 3- and 4-substituted eta(4)-(1Z)-(sulfinyldienal)iron(0) tricarbonyl complexes is dependent on the nature of the alkyl substituent. For 1-sulfinyl-1,3-pentadien-5-al iron complexes (11a-d), the aldehyde predominately reacts through the s-cis conformer, with diastereoselectivites as high as 95:5 (for homoallylic alcohol 13d). For 3-formyl-1-sulfinyl-1,3-butadiene iron complexes (12a,b), the aldehyde predominately reacts through the s-trans conformer (diastereomer ratio for homoallylic alcohol, 14b, 89:11).

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页码：1841 / 1849

页数：9

相关论文

共 19 条

[1] PREPARATION OF TRICARBONYL(ETA-4-VINYLKETENE)IRON(0) COMPLEXES FROM TRICARBONYL(ETA-4-VINYL KETONE)IRON(0) COMPLEXES AND THEIR SUBSEQUENT CONVERSION TO TRICARBONYL(ETA-4-VINYLKETENIMINE)IRON(0) COMPLEXES [J].

ALCOCK, NW ;

RICHARDS, CJ ;

THOMAS, SE .

ORGANOMETALLICS, 1991, 10 (01) :231-238

[2] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[3] Chiral sulfinyl-1,3-dienes. Synthesis and use in asymmetric reactions [J].

Aversa, MC ;

Barattucci, A ;

Bonaccorsi, P ;

Giannetto, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1339-1367

[4] 4-[(TERT-BUTYLDIPHENYLSILYL)OXY]-2-(TRIBUTYLSTANNYL)-(E)-2-BUTEN-1-OL - A USEFUL PRECURSOR FOR TETRAHYDROFURAN SYNTHESIS [J].

BARRETT, AGM ;

BARTA, TE ;

FLYGARE, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4246-4249

[5] Total synthesis of (+)-dysidiolide [J].

Boukouvalas, J ;

Cheng, YX ;

Robichaud, J .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02) :228-229

[6] GEOMETRICAL REACTION COORDINATES .2. NUCLEOPHILIC ADDITION TO A CARBONYL GROUP [J].

BURGI, HB ;

DUNITZ, JD ;

SHEFTER, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :5065-5067

[7] STEREOCHEMISTRY OF REACTION PATHS AT CARBONYL CENTERS [J].

BURGI, HB ;

DUNITZ, JD ;

LEHN, JM ;

WIPFF, G .

TETRAHEDRON, 1974, 30 (12) :1563-1572

[8] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[9] STABILIZATION OF HYPERACTIVE MOLECULES BY COMPLEXATION - 2-FORMYLBUTADIENE OF IRON-TRICARBONYL - PREPARATION, DIVIDING AND REACTIVITY [J].

FRANCKNEUMANN, M ;

MARTINA, D ;

HEITZ, MP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (01) :61-77

[10] STEREOSELECTIVE SYNTHESIS OF 1,4-DIENES - APPLICATION TO THE PREPARATION OF INSECT PHEROMONES (3Z,6Z)-DODECA-3,6-DIEN-1-OL AND (4E,7Z)-TRIDECA-4,7-DIENYL ACETATE [J].

HUTZINGER, MW ;

OEHLSCHLAGER, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4595-4601