Synthesis of the First Chiral, Functionalised‐Bridged Resorcinarenes in Asymmetric Catalysis: Evidence for Intracavity Asymmetric Catalysis

Arnott, Gareth E.; Heaney, H.; Hunter, Roger; Page, Philip C. Bulman

doi:10.1002/ejoc.200400615

Cited by 25 publications

(9 citation statements)

References 42 publications

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“…The study of synthetic modeling systems for chiral recognition is an area of ever‐increasing research activity. Such model systems can find potential applications in the development of pharmaceuticals, enantioselective catalysis, separation, analysis of enantiomers, fundamental host–guest chemistry, and supramolecular material science . They can also contribute to better understanding of biological systems and their functions because chiral recognition is an essential phenomenon in living systems.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Highly Enantioselective Fluorescent Recognition of α‐Aminocarboxylic Acid Anions Using Chiral Oxacalix[2]arene[2]bisbinaphthes

Jiao

Yao

et al. 2012

Chirality

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The triazine-based bisbinaphthyl crown ethers oxacalix[2]arene[2]bisbinaphthes R-1, R-2, R-3 and S-1, S-2, S-3 were synthesized. The interactions of these compounds with various α-aminocarboxylic acid anions were studied. The crown ethers were found to carry out highly enantioselective fluorescent recognition of α-aminocarboxylic acid anions. It is observed that within a certain concentration range, one enantiomer of the chiral α-aminocarboxylic acid anions can increase the fluorescence intensity of the crown ethers by fivefold to sixfold, whereas the other enantiomer scarcely enhances the fluorescence. Such unusually high enantioselective responses make these crown ethers very attractive as fluorescent sensors in determining the enantiomeric composition of α-aminocarboxylic acid anions.

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Section: Introductionmentioning

confidence: 99%

Syntheses and Highly Enantioselective Fluorescent Recognition of α‐Aminocarboxylic Acid Anions Using Chiral Oxacalix[2]arene[2]bisbinaphthes

Jiao

Yao

et al. 2012

Chirality

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“…Treatment of acetonedicarboxylic acid 19 with TMSO(CH 2 ) 3 OTMS in the presence of a catalytic amount of TMSOTf yielded 20 . 14 Exposure of 20 to MeMgBr in CH 2 Cl 2 at −78 °C for 12 h afforded keto ester 21 in moderate conversion, but we were able to recover the unreacted starting material. Dieckmann condensation of 21 promoted by LDA provided 2b in a similar fashion to the cyclization of 7 to 2a .…”

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confidence: 80%

Asymmetric Total Syntheses of (−)-Variabilin and (−)-Glycinol

Calter

2011

Org. Lett.

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Total syntheses of (−)-variabilin and (−)-glycinol have been accomplished, using the catalytic, asymmetric “interrupted” Feist-Bénary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products in over 90% ee in both cases. Other key steps include an intramolecular Buchwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.

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“…His work on steroid chemistry led to the acquiring of several Patents, one on estrogenically active agents (Bull et al, 1988), another on ethanoestratrienes as estrogens and contraceptives (Kirsch et al, 1990), and a third on alkylated estradiols (Bull et al, 1995). Hunter's group continues to develop new methodology in organic synthesis (Hutchings & Hunter, 1990;Hunter & Bartels, 1991;Bartels & Hunter, 1993;Hunter et al, 1998;Arnott et al, 2004). Organometallic and co-ordination compounds for use as catalysts or liquid crystals have been under active study (Friedrich & Moss, 1991;Foulds et al, 1994;Gafoor et al, 1996;Yin & Moss, 1999;Cromhout & Hutton, 2000), and computer methods are now applied to predicting the structure and properties of polymer systems (Naidoo et al, 1997Kuttel & Naidoo, 2005); a successful international conference on computational chemistry was hosted in 2005.…”

Section: Other Major Research Programmes In the Modern Eramentioning

confidence: 97%

A history of the Chemistry Department, University of Cape Town

Stephen¹

2005

Transactions of the Royal Society of South Africa

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includes material from its inception in 1876 until the closing years of the millennium preceding 1999. Several phases of growth are presented: first, as a one-man enterprise, Professor Paul Daniel Hahn introduced the teaching of Chemistry and fostered both pure and applied research; this developed with the founding of the University of Cape Town at the end of World War 1. A move into the new building at Groote Schuur followed, with a rapid expansion on many fronts after World War II. Apart from a brief interlude as a School comprising four separate Departments (1974)(1975)(1976)(1977)(1978)(1979)(1980)(1981)(1982)(1983)(1984)(1985)(1986)(1987)(1988), the Department of Chemistry continued to grow in terms of student numbers, courses offered, and productivity of its research groups, until the present time. The Department has occupied a large building, named after its first full-time professor, since 1972. Advances in performance, consequent on improved, computerised instrumentation and teaching techniques, are evident.

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Synthesis of the First Chiral, Functionalised‐Bridged Resorcinarenes in Asymmetric Catalysis: Evidence for Intracavity Asymmetric Catalysis

Cited by 25 publications

References 42 publications

Syntheses and Highly Enantioselective Fluorescent Recognition of α‐Aminocarboxylic Acid Anions Using Chiral Oxacalix[2]arene[2]bisbinaphthes

Syntheses and Highly Enantioselective Fluorescent Recognition of α‐Aminocarboxylic Acid Anions Using Chiral Oxacalix[2]arene[2]bisbinaphthes

Asymmetric Total Syntheses of (−)-Variabilin and (−)-Glycinol

A history of the Chemistry Department, University of Cape Town

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