Metal-induced rearrangements and insertions into cyclopropyl olefins

Sarel, Shalom

doi:10.1021/ar50125a005

Cited by 80 publications

(31 citation statements)

References 31 publications

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“…The credit for the development and application of organoiron complexes in organic and organometallic chemistry can be ascribed to brilliant contributions by Fischer [ 32 , 33 ], Pettit [ 34 ], Müller [ 35 ], Alper [ 10 ], King [ 36 ], Rosenblum [ 37 – 40 ], Brunner [ 41 ], Birch [ 14 ], Collman [ 42 ], Gompper [ 43 ], Sarel [ 44 ], Noyori [ 45 , 46 ], Pearson [ 20 , 21 ], Casey [ 47 ], Hegedus [ 13 ], Wojcicki [ 48 ], Reger [ 49 ], Helquist [ 50 ], Gladysz [ 51 ], Kerber [ 52 ], Wulff [ 53 ], Ojima [ 54 ], Negishi [ 55 ], Backvall [ 56 ], Herndon [ 57 ], von Gustorf [ 58 ], Grée [ 30 ], Seyferth [ 59 ], Davies [ 60 – 63 ], Liebeskind [ 64 ], Semmelhack [ 65 ], Brookhart [ 66 ], and others [ 31 , 67 – 73 ]. Credit is also due Fischer [ 24 ], Dötz [ 74 ], Jaouen [ 18 ], Semmelhack [ 19 ], Wulff [ 53 , 75 ] Hegedus [ 76 ], Yamashita [ 77 ], and others [ 77a , 77b ] for their st...…”

Section: Scope Of the Reviewmentioning

confidence: 99%

“…A brief overview of reactions of cyclopropane derivatives in the presence of iron pentacarbonyl, Fe(CO) 5 , or its dimer Fe 2 (CO) 9 , is included for continuity. This exciting chemistry has been studied by Sarel, and many metal-induced rearrangements of, and insertions into, cyclopropyl alkenes have been reviewed by that author [ 44 ].…”

Section: Iron-catalyzed Synthesis and Some Reactions Of Cyclopropamentioning

confidence: 99%

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New chemical and stereochemical applications of organoiron complexes

Fatiadi

1991

J. RES. NATL. INST. STAN.

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The objective of this review is to provide a current overview of the rapidly developing chemistry of organometallic complexes and particularly organoiron complexes useful in asymmetric and stereoselective reactions. Also covered are stereoselective reactions of α, β-unsaturated acyl ligands bound to the chiral auxiliary [(η5-C5H5) Fe(CO)(PPh3)] and new applications of organoiron complexes in the synthesis of natural products. The mechanistic aspects and stabilizing effects of the Fe(CO)3 group for alkenes or conjugated dienes are discussed. A brief summary of recent work on the special role of iron in biological reactions is also included.

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Section: Scope Of the Reviewmentioning

confidence: 99%

Section: Iron-catalyzed Synthesis and Some Reactions Of Cyclopropamentioning

confidence: 99%

New chemical and stereochemical applications of organoiron complexes

Fatiadi

1991

J. RES. NATL. INST. STAN.

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“…Iron carbonyls can etlect a variety of fascinating ring-opening and cyclization reactions of vinyl cyclopropanes; a review was published by Sarel" in 1978. Since the appearance of the review, Sarel and coworkers" described the photolytic reaction of iron pentacarbonyl and trans-l-propenyl-4-methylenespiro [2.x]alkanes (X = 4-6) to give isomeric cyclooctadienones and several iron carbonyl complexes. (T, '7T-Complexes, obtained by irradiation of tricyclic vinylcyclopropanes and Fe(CO)" can be oxidatively cleaved to ethers or lactones."…”

Section: B Vinyl Cyc1opropanesmentioning

confidence: 99%

“…In the example cited, oxidative cydlization of 13 by eerie ion in acetonitrile gave the f3-lactone (15) in 51% yield and the 8-lactone (16) in 29% yield. However, only the 8-lactone was formed (75% yield) from eerie ion treatment of the anti complex (14). Another important example is the stereospecific eerie ion induced conversion of the isomeric complexes 17 and 19 to the trans and cis-f3-lactones, 18 and 20, respectively."…”

Section: A Simple Epoxidesmentioning

confidence: 99%

“…Irradiation of vinyl epoxides with iron pentacarbonyl in benzene gives ferrelactone complexes in good yields. For instance, photolysis of 1,2-epoxy-l-vinylcyclopentane and Fe(CO)s afforded the syn (13) and anti (14) ferrelactones in 64% and 11% yields, respectively.f:" In other words, the reaction is not stereo- The lactone complexes can be converted to lactam analogs by treatment with an amine in the presence of zinc chloride. An important example is the reaction of 12 with the protected amino acid 22 to form the lactam 23 in 81% yield.…”

Section: B Vinyl Epoxidesmentioning

confidence: 99%

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The Cleavage of Three‐Membered Ring Compounds by Transition Metal Organometallic Complexes

Alper¹

1981

Israel Journal of Chemistry

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Transition metal organometallic complexes effect a wide range of useful and interesting cleavage reactions of three‐membered ring compounds. This review examines some recent developments in the organometallic chemistry of cyclopropanes, epoxides, episulfides and azirines. Novel synthetic approaches to heterocyclic [e.g., β γ and δ‐lactones, β‐lactams, isoxazoles, pyrazoles, indoles] and acyclic compounds [β‐diketones, vinyl isocyanates] have been achieved by means of these cleavage reactions.

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The Vinylcyclopropane–CyclopenteneRearrangement

1985

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The vinylcyclopropane‐cyclopentene isomerization was discovered in 1959. After the mechanism was studied in detail, this rearrangement was incorporated into many useful synthetic schemes. Various heterocyclic permutations of the vinylcyclopropane system have also been investigated, yielding several synthetic methods based on the rearrangements of cyclopropyl ketones and cyclopropyl imines to dihydrofurans and dihydropyrroles, respectively. This chapter is concerned only with the rearrangements of vinylcyclopropanes to cyclopentenes. Excluded are Cope rearrangements of divinylcyclopropanes and rearrangements of cyclopropyl compounds not leading to cyclopentenes. The isomerization of 2,2‐dichlorovinylcyclopropane was described in 1959. The rearrangement of the parent hydrocarbon was reported independently by two laboratories a year later. Although no prior mention of this rearrangement exists in the literature, it appears likely that it occured unobserved as early as 1922 during the preparation of vinylcyclopropane by drastic methods. The presence of cyclopentene in the reaction mixtures resulting from the Hofmann elimination of a β‐cyclopropylethylammonium salt is a likely possibility, considering the low temperature at which vinylcyclopropane rearranges. The detection and identification of reaction products by refractive indices only may have prevented recognition of the isomerization at that time. During the decade following the discovery of the rearrangement, virtually every simple vinylcyclopropane was studied in an attempt to settle the question of biradical versus concerted mechanism. Later there was intense activity in the applications of this rearrangement and many of its analogs to organic synthesis. Studies have also emphasized transition‐metal‐catalyzed rearrangements of vinylcyclopropanes.

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Metal-induced rearrangements and insertions into cyclopropyl olefins

Cited by 80 publications

References 31 publications

New chemical and stereochemical applications of organoiron complexes

New chemical and stereochemical applications of organoiron complexes

The Cleavage of Three‐Membered Ring Compounds by Transition Metal Organometallic Complexes

The Vinylcyclopropane–CyclopenteneRearrangement

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