The Reformatsky Reaction with Benzalaniline

Gilman, Henry; Speeter, Merrill E.

doi:10.1021/ja01251a503

Cited by 141 publications

(45 citation statements)

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“…Commonly, the lactam ring is formed through either ketene–imine cyclizations (another ketene application pioneered by Staudinger)58 or ester enolate–imine condensations59 (the Gilman–Speeter reaction). However, other notable methods are sometimes employed, including photoinduced rearrangements60 and radical cyclizations 61.…”

Section: Asymmetric β-Lactam Synthesismentioning

confidence: 99%

Catalytic, asymmetric reactions of ketenes and ketene enolates

2009

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Section: Asymmetric β-Lactam Synthesismentioning

confidence: 99%

Catalytic, asymmetric reactions of ketenes and ketene enolates

2009

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“…The ester enolate-imine condensation, also called Gilman-Speeter reaction, is another well-accepted method for b-lactam synthesis (Scheme 4) [67][68][69]. In 1997, Tomioka reported the first example of a direct catalytic enantioselective synthesis of b-lactam by using this method [70].…”

Section: Solid-phase Techniques For B-lactam Synthesismentioning

confidence: 99%

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Mandal

Ghosh

Basu

2010

Heterocyclic Scaffolds I

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Since the discovery of penicillin in 1929, b-lactam antibiotics have been recognized as potentially chemotherapeutic drugs of incomparable effectiveness, conjugating a broad spectrum of activity with very low toxicity. The primary motif azetidin-2-one ring (b-lactam) has been considered as specific pharmacophores and scaffolds. With the advent of combinatorial chemistry and automated parallel synthesis coupled with ample interests from the pharmaceutical industries, recent trends have been driven mostly by adopting solid phase techniques and polymersupported synthesis of b-lactams. The present survey will present an overview of the developments on the polymer-supported and solid phase techniques for the preparation of b-lactam ring or b-lactam containing antibiotics published over the last decade. Both unsubstituted and substitutions with different functional groups at various positions of b-lactams have been synthesized using solid phase technology. However, Wang resin and application of Staudinger [2+2] cycloaddition reaction have remained hitherto the major choice. It may be expected that other solid phase approaches involving different resins would be developed in the coming years.

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“…[1] Since its original discovery, [2] this reaction has been constantly refined to become a powerful and reliable synthetic tool. [1] Since its original discovery, [2] this reaction has been constantly refined to become a powerful and reliable synthetic tool.…”

Section: Introductionmentioning

confidence: 99%