Catalytic Diastereoselective Synthesis of Cis-1,2-Disubstituted Cyclopropanols from Esters Using a Vicinal Dicarbanion Equivalent

Corey, E. J.; Rao, S. A.; Noe, Mark C.

doi:10.1021/ja00099a068

Cited by 168 publications

(78 citation statements)

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“…Typically, vicinal coupling between trans protons for the cyclopropyl ring show a coupling of 4.2-5.9 Hz, compared to 8.4-9.7 Hz for protons in a cis relationship (16,17). Thus the vicinal coupling of 6.3 Hz observed for H(3a) and 9.8 Hz for H(3b) with the C(2) proton placed H(3a) in a trans and H(3b) in a cis orientation to H(2).…”

Section: Purification Of the Neurotoxinmentioning

confidence: 99%

Diplonine, a Neurotoxin Isolated from Cultures of the Fungus Stenocarpella maydis (Berk.) Sacc. that Induces Diplodiosis

Snyman

Kellerman

Vleggaar

et al. 2011

J. Agric. Food Chem.

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Diplodiosis is a neuromycotoxicosis of cattle and sheep caused by ingestion of maize infected with the ear-rot fungus Stenocarpella (= Diplodia) maydis. Apart from ataxia, paresis and paralysis, the toxin is responsible for stillbirths and neonatal losses characterized by the presence of spongiform degeneration in the white matter of the brain in the offspring of dams exposed to infected maize cobs. In the present study a toxin, named diplonine, which induced neurological signs in guinea pigs resembling some of those occurring in cattle and sheep, was isolated from S. maydis cultures. Purification of diplonine was achieved by methanol extraction followed by chromatographic separation on silica gel and RP-18 stationary phases. The structure and relative configuration of diplonine was defined by analysis of NMR and MS data as (S)-2-amino-2-[(1R,2S)-1-hydroxy-2-methylcyclopropyl]acetic acid or the (S)-2-amino-2-[(1S,2R)-diastereomer.

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Section: Purification Of the Neurotoxinmentioning

confidence: 99%

Diplonine, a Neurotoxin Isolated from Cultures of the Fungus Stenocarpella maydis (Berk.) Sacc. that Induces Diplodiosis

Snyman

Kellerman

Vleggaar

et al. 2011

J. Agric. Food Chem.

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“…Thus, it seemed as if only an ethyl titanium species would undergo a rapid β-H elimination to give the titanacyclopropane 5 -the Kulinkovich reagent. However, with chloro titanium trisisopropoxide as the titanium(IV)source also higher substituted organomagnesium compounds (equation 2) could be applied to give substituted titanacyclopropane intermediates [4]. This finding largely extended the preparative value of this cyclopropanation reaction.…”

Section: Reaction Scope and Limitationmentioning

confidence: 95%

“…A first step towards an asymmetric catalysis of the Kulinkovich reaction has been undertaken by Corey [4]. Thus, reaction of ethylacetate with two equivalents of phenethyl magnesium bromide in the presence of 30 mol% of a TADDOLbased titanium reagent gave the cyclopropanol 30 in 70% ee (equation 9).…”

Section: Control Of Absolute Configurationmentioning

confidence: 99%

“…Scheme 1 EtMgBr/Ti(Oi-Pr) 4 -the Kulinkovich reagent: Synthetic equivalent of a two-carbon-1,2-dianion synthon Not surprisingly, soon after Kulinkovich's discovery this reaction has attracted worldwide a number of research groups which has lead to the development of a variety of useful synthetic methods. The purpose of this article is to provide the reader with a brief overview of the current state of this rapidly developing area of synthetic organic chemistry based on the Kulinkovich reagent.…”

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confidence: 99%

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Bis alkoxytitanacyclopropanes and -propenes (Kulinkovich reagents): Versatile reagents for carbon—carbon bond formation

Breit¹

2000

J. prakt. Chem.

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“…To this end, the use of a chiral titanium complex was successful. [9] An alternative approach is to incorporate a chiral auxiliary in…”

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confidence: 99%

Highly Enantio- and Diastereoselective Synthesis of 2-Substituted 1-Bicyclo[3.1.0]hexanols

Mizojiri

Urabe

Sato

1998

Angewandte Chemie International Edition

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Catalytic Diastereoselective Synthesis of Cis-1,2-Disubstituted Cyclopropanols from Esters Using a Vicinal Dicarbanion Equivalent

Cited by 168 publications

References 0 publications

Diplonine, a Neurotoxin Isolated from Cultures of the Fungus Stenocarpella maydis (Berk.) Sacc. that Induces Diplodiosis

Diplonine, a Neurotoxin Isolated from Cultures of the Fungus Stenocarpella maydis (Berk.) Sacc. that Induces Diplodiosis

Bis alkoxytitanacyclopropanes and -propenes (Kulinkovich reagents): Versatile reagents for carbon—carbon bond formation

Highly Enantio- and Diastereoselective Synthesis of 2-Substituted 1-Bicyclo[3.1.0]hexanols

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