Enantioselective Synthesis and Stereoselective Ring Opening of <i>N</i>‐Acylaziridines

Cockrell, Jennifer; Wilhelmsen, Christopher A.; Rubin, Heather N.; Martin, Allen; Morgan, Jeremy B.

doi:10.1002/anie.201204224

Cited by 62 publications

(30 citation statements)

References 89 publications

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“…Apart from the application of biomolecular detection, chiral catalysis is another important region. Chiral catalysis is an effective approach to yield a chiral product, or to differentiate between the two enantiomers of a racemic mixture . Metal NPs are potentially catalytically active and can also be used as catalyst supports.…”

Section: Applicationsmentioning

confidence: 99%

Plasmonic Circular Dichroism of Gold Nanoparticle Based Nanostructures

Meng

Lin

et al. 2019

Advanced Optical Materials

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IntroductionChirality refers to the certain handedness in geometry with a mirror image that cannot coincide with itself. [1] Mirror images with opposite chirality are enantiomers, and can be divided into left-and right-handedness, respectively. Two enantiomers can interact differently with left-(LCP) and right-circularly With great advances in wet chemical synthesis of nanoparticles (NPs), plasmonic NPs with various sizes and morphologies are easily available nowadays and demonstrate great potentials in optical, electronic, and biomedical applications. Plasmonic circular dichroism (CD), relating to circular dichroism responses at localized surface plasmon resonance of metal nanostructures, has emerged as a research direction of plasmonics with promising prospects in enantioselective catalysis, chiral separation, and ultrasensitive detections. Herein, plasmonic CD responses of gold nanoparticle based nanostructures are summarized. Two kinds of plasmonic CD phenomena are investigated: structural CD and induced CD. Structural CD is the response from chiral assemblies composed of plasmonic NPs with strong dipole-dipole interactions. Induced CD is the response of nonchiral plasmonic NPs with chiral molecules attached at surface. The weak CD is the result of Coulomb interaction between chiral molecules and plasmonic NPs. Efforts on how to achieve strong CD signals for these two configurations by using chiral molecules and Au nanoparticles are reported. The fabrication of chiral nanostructures, tuning and amplification of CD responses, CD-based biosensors, chiral catalysis, and future perspectives are presented. The importance of the shape anisotropy of gold nanorods in the generation and amplification of CD signals is especially highlighted.

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Section: Applicationsmentioning

confidence: 99%

Plasmonic Circular Dichroism of Gold Nanoparticle Based Nanostructures

Meng

Lin

et al. 2019

Advanced Optical Materials

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“…21 The synthesis of a β-substituted tryptamine ( 3 ) from a mono-substituted aziridine has only been reported in low yields for carbamate-protected aziridines; 21,42 however, limited examples with alternative nitrogen protecting groups are known. 33,43 This report details our discovery that PNZ-protected, alkyl substituted aziridines ( 4 ) undergo selective ring opening by C2 attack with indoles to produce β-substituted tryptamines ( 5 ). 7,44,45 The tryptamine products can be readily functionalized at nitrogen after PNZ removal under mild conditions.…”

Section: Introductionmentioning

confidence: 78%

“…The PNZ-protected tryptamine ( 7 ) was isolated in 71% yield as a single enantiomer as confirmed by HPLC 46 Excess indole was employed, based on previous data, to maximize tryptamine yield. 33 …”

Section: Resultsmentioning

confidence: 99%

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Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines

2016

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Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce β-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.

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“…On the basis of a known procedure, 3 c was successfully converted into the chiral oxazoline 5 , which could further yield chiral amino alcohols (Scheme a). The reaction of 3 c with hydrogen chloride in THF gave the β‐chloro‐α‐aminoketone 6 in good yield (Scheme b) . In contrast, the transformation of the tosylated aziridine intermediate 7 , prepared from 3 a , led to the β‐amino‐α‐hydroxyketone 8 (Scheme c) …”

Section: Figurementioning

confidence: 99%