Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes

Hegedus, Louis S.; Imwinkelried, René; Alarid-Sargent, M.; Dvořák, Dalimil; Satoh, Yoshitaka

doi:10.1021/ja00159a034

Cited by 108 publications

(47 citation statements)

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“…The products prepared by the above procedure were characterized spectroscopically as shown below. 6 13.3, 19.9, 29.5, 39.9, 63.4, 64.7, 126.1, 127.0, 127.2, 128.3, 128.6, 128.8, 134.9, 137.4, 167.8 117.1, 123.9, 125.8, 127.3, 127.8, 128.6, 128.9, 129.0, 129.2, 134.6, 137.3, 137.4, 165.5; MS mlz (relative intensity) 299 (M+, 2), 180 (loo), 165 (17), 104 (3), 77 (25), 51 (12). Anal.…”

Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Synthesis of β-Lactams via Carbonylative Cycloaddition of Benzyl and Allyl Halides with Imines

Cho

Jiang

Shim

1999

Synthetic Communications

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Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Synthesis of β-Lactams via Carbonylative Cycloaddition of Benzyl and Allyl Halides with Imines

Cho

Jiang

Shim

1999

Synthetic Communications

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“…A vast array of imines, including simple imines, a-iminoketones, a-diimines, iminodithiocarbonates, and ferrocene imines [52], can be used. The asymmetric version of this route can be accomplished on using enantiopure chromium carbenes, such as the (R)-phenylglycine derivative 17, which allowed the preparation of optically active b-lactams 18 (Scheme 24.7) [53]. A theoretical-experimental approach to the mechanism of the photocarbonylation of chromium(0) (Fischer)-carbene complexes and their reaction with imines to give b-lactams has been published [54].…”

Section: Chromium Carbene-imine Cyclizationmentioning

confidence: 99%

The Chemistry of 2‐Azetidinones (β‐Lactams)

Alcaide¹,

Almendros²,

Luna³

2011

Modern Heterocyclic Chemistry

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The large number of recent reports on b-lactam chemistry demonstrates the increasing interest in this important class of compounds. Monocyclic b-lactams frequently serve as precursors for the synthesis of classical bicyclic b-lactam antibiotics. The cyclic 2-azetidinone skeleton has been extensively used as a template on which to build the heterocyclic structure fused to the four-membered ring, using the chirality and functionalization of the b-lactam nucleus as a stereocontrolling element. The discovery of nonclassical b-lactam antibiotics, such as monobactams and nocardicins, coupled with ever-growing new applications such as enzyme inhibition has triggered a renewed interest in the building of new monocyclic b-lactam derivatives. Besides the utility of b-lactams as biologically active agents, they are used as intermediates in a-and b-amino acid synthesis, as well as building blocks for alkaloids, heterocycles, taxoids and other types of compounds of biological and medicinal interest. Physicochemical Data Computational ChemistryTheoretical studies show that b-lactams are weaker bases, in the gas phase, than acyclic amides [1]. The attenuation of basicity upon cyclization is stronger than that found for cyclic ketones of similar size due to the existence of a negative hyperconjugation effect that is present in b-lactams but not in cyclic ketones. Ab initio calculations indicate that both b-lactams and acyclic amides are oxygen bases, but the gap between the oxygen and nitrogen intrinsic basicities is much smaller in the former due to the aforementioned cyclization effects. This decrease of the oxygen Modern Heterocyclic Chemistry, First Edition. Edited

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“…Some ␤-lactam derivatives have also been recognized as inhibitors of human leukocytase elastase [6] and serine protease [7,8]. Till now, numerous ␤-lactam derivatives of thiazoline and dihydrothiazine, containing a fiveand six-membered sulfur and nitrogen-containing heterocyclic ring, respectively, have been synthesized by various methods [9][10][11]. In recent years, our working group has paid much attention to the synthesis and stereostructure investigation of tricyclic derivatives of benzothiazepines and benzodiazepines because of their potential biological and pharmaceutical importance [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Stereospecific synthesis of azeto[2,1‐d]‐ [1,5]benzothiazepin/diazepin‐1‐ones

Huang

2003

Heteroatom Chemistry

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Abstract2a,4‐Disubstituted 2‐phenoxy‐2,2a,3,4‐tetrahydro‐1H‐azeto[2,1‐d][1,5]benzothiazepin‐1‐ones and 5‐benzoyl‐2‐phenoxy‐2a,3,4,5‐tetrahydro‐azeto[1, 2‐a][1,5]benzodiazepin‐1(2H)‐ones were synthesized in moderate to good yields by stereospecific Staudinger cycloaddition reactions of 2,4‐disubstituted 2,3‐dihydro‐1,5‐benzothiazepines and 1‐benzoyl‐2,3‐dihydro‐1H‐1,5‐benzodiazepines, respectively, with phenoxy acetyl chloride in the presence of triethylamine in anhydrous benzene. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:564–569, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10196

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Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes

Cited by 108 publications

References 1 publication

Palladium-Catalyzed Synthesis of β-Lactams via Carbonylative Cycloaddition of Benzyl and Allyl Halides with Imines

Palladium-Catalyzed Synthesis of β-Lactams via Carbonylative Cycloaddition of Benzyl and Allyl Halides with Imines

The Chemistry of 2‐Azetidinones (β‐Lactams)

Stereospecific synthesis of azeto[2,1‐d]‐ [1,5]benzothiazepin/diazepin‐1‐ones

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