Three-Membered-Ring-Based Molecular Architectures

Meijere, Armin de; Kozhushkov, Sergei I.; Schill, Heiko

doi:10.1021/cr0505369

Cited by 146 publications

(62 citation statements)

References 730 publications

(1,257 reference statements)

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“…Aliphatic perfluorocarbon chains are known to adopt a helical structure in the crystalline state and in solution as a result of electrostatic repulsion of the fluorine substituents in the 1-and 3-positions, [2] poly(ethyleneglycol) adopts a helical conformation in isobutyric acid solution, [3] and permethyldecasilane forms a helix in a helical schizophyllan matrix. [4] As formally saturated hydrocarbons have no driving forces to adopt helical conformations (apart from van der Waals interactions), their conformations range from "zig-zag" for linear hydrocarbons on one hand to helical for certain enantiomerically pure [n]triangulanes (1) [5,6] on the other. Helicity of the latter, however, is predetermined by their rigid helical shape.…”

Section: Dedicated To Professor Kenneth B Wiberg On the Occasion Of mentioning

confidence: 99%

1,1′‐Linked Cyclopropane Derivatives: The Helical Conformation of Quinquecyclopropanol

et al. 2007

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In a twist: 1,1′‐Linked oligocyclopropanols have been obtained by an iterated reaction of a cyclopropaneboronate with in situ generated lithium bromocyclopropylidenoid and subsequent oxidation. As predicted by DFT computations for sexicyclopropane (shown in blue) in the gas phase, the quinquecyclopropane unit in the 3,5‐dinitrobenzoate of quinquecyclopropanol (yellow, dinitrobenzoyl group omitted for clarity) adopts a helical conformation in the crystal.

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Section: Dedicated To Professor Kenneth B Wiberg On the Occasion Of mentioning

confidence: 99%

1,1′‐Linked Cyclopropane Derivatives: The Helical Conformation of Quinquecyclopropanol

et al. 2007

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“…The thermal methylene-or alkylidenecyclopropane rearrangement consists in a [1,3]-sigmatropic transformation between two methylene-or alkylidenecyclopropanes. De Meijere et al studied the thermal rearrangement of bicyclopropylidene 59 into methylene-A C H T U N G T R E N N U N G spiropentane 237, as depicted in Scheme 79.…”

Section: Rearrangementsmentioning

confidence: 99%

“…[1] Indeed, organic chemists have always been fascinated by the cyclopropane subunit, [2] which has played and continues to play a prominent role in organic chemistry. Its strained structure, interesting bonding characteristics, and value as an internal mechanistic probe have attracted the attention of the physical organic community as well.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Methylene‐ and Alkylidenecyclopropane Derivatives

Audran

Pellissier

2010

Adv Synth Catal

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Since the methylenecyclopropane moiety is found in many biologically active natural substances, the synthesis of methylene-and alkylidenecyclopropanes remains a considerable challenge. In addition, an attractive feature is their surprising stability, accompanied by a high level of strain, conferring on them an otherwise unattainable chemical reactivity. The growing interest in the chemistry of these compounds has in its turn stimulated the development of alternative approaches to their skeleton, aimed at selectively introducing structural and chemical diversification. The three principal methods to synthesize these important compounds are based on the formation of the cyclopropane ring, the use of preformed cyclopropanes, and the use of preformed methyleneand alkylidenecyclopropanes.

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“…[12] Another interesting group of completely rigid skeletons that comes to mind as a potential ligand platform includes the highly strained so-called linear [n]triangulanes 3, hydrocarbons that consist of spiroannelated cyclopropane rings only. [13] Herein we describe the realization of this idea and present the design of a new type of chiral bidentate diphosphane ligands represented by 4-6 (n = 2, 3) featuring rigid triangulanyl backbones, which might lead to novel, highly efficient catalytic systems for various reactions.…”

Section: Introductionmentioning

confidence: 99%

A Novel Type of Chiral Triangulane‐Based Diphosphane Ligands for Transition Metals

et al. 2012

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A new original strategy for the synthesis of axially and helically chiral bidentate diphosphane ligands featuring a rigid triangulanyl backbone has been elaborated and executed for several representative enantiomerically pure ligands. Thus,(1R,3S,4S)‐1,4‐bis[(diphenylphosphanyl)methyl]spiro[2.2]pentane [(1R,3S,4S)‐24·(BH3)2], [(1R,3R,4S)‐4‐(diphenylphosphanyl)methylspiro[2.2]pentan‐1‐yl]diphenylphosphane [(1R,3R,4S)‐27·(BH3)2], [(1R,3R,4S,5R)‐5‐(diphenylphosphanyl)methyldispiro[2.0.2.1]heptan‐1‐yl]diphenylphosphane [(1R,3R,4S,5R)‐30·(BH3)2], (1S,3S,4S)‐1,4‐bis(diphenylphosphanyl)spiropentane [(1R,3S,4S)‐35·(BH3)2], (1S,3S,4S)‐1,4‐bis(diphenylphosphanyl)spiropentane [(1S,3S,4S)‐35·(BH3)2], (1S,3S,4S)‐1,4‐bis(diphenylphosphanyl)spiropentane [(1R,3R,4S)‐35·(BH3)2], and (1R,3R,4R,5R)‐1,5‐bis(diphenylphosphanyl)dispiro[2.0.2.1]heptane [(1R,3R,4R,5R)‐36·(BH3)2] with a spiropentyl and a dispiro[2.0.2.1]heptyl moiety, respectively, have been prepared as bishydroborane complexes applying repetitively the same set of standard synthetic operations, starting from [(1S,3R)‐4‐methylenespiropent‐1‐yl]methyl acetate [(1S,3R)‐7], (4,4‐dibromospiropent‐1‐yl)methanols [(1S,3R)‐8 and (1R,3S)‐8] and (dibromodispiro[2.0.2.1]heptyl)methanols (1R,3S,4R)‐9, (1S,3R,4S)‐9 and (1S,3R,4R)‐9 in 4–7 steps. The relative configurations of all important intermediates as well as the absolute configurations of the key intermediates and most final products were established by X‐ray crystal structure analyses.

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Three-Membered-Ring-Based Molecular Architectures

Cited by 146 publications

References 730 publications

1,1′‐Linked Cyclopropane Derivatives: The Helical Conformation of Quinquecyclopropanol

1,1′‐Linked Cyclopropane Derivatives: The Helical Conformation of Quinquecyclopropanol

Synthesis of Methylene‐ and Alkylidenecyclopropane Derivatives

A Novel Type of Chiral Triangulane‐Based Diphosphane Ligands for Transition Metals

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