Facile Synthesis of Selenium‐Containing Bicyclic β‐Lactams through Enyne Metathesis

Bankar, Deepali B.; Koketsu, Mamoru

doi:10.1002/ejoc.201000055

Cited by 13 publications

(3 citation statements)

References 28 publications

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“…95,97 Larger B rings were made with selenium present in the nascent ring using the second-generation Grubbs catalyst (equation 34). 96 This reaction proved quite challenging due to the ring size and the presence of the selenium atom (see Section 5.27.3.4 for an example of sulfur in CEYM). Neither the first-generation Grubbs carbene or lower reaction temperatures were sufficient to promote this Table 10) possibly due to alkyne polymerization under the forcing reaction conditions.…”

Section: Ring-closing Enyne Metathesis With Ruthenium Carbenesmentioning

confidence: 99%

5.27 Ene–Yne Metathesis

Diver

Clark

2014

Comprehensive Organic Synthesis II

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Section: Ring-closing Enyne Metathesis With Ruthenium Carbenesmentioning

confidence: 99%

5.27 Ene–Yne Metathesis

Diver

Clark

2014

Comprehensive Organic Synthesis II

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“…34 compounds 52b-52d, respectively, in good yields, however, an attempt to bring about the cyclization of 51a in the presence of the Grubbs 2 nd gen. catalyst (10 mol%) was failed (Scheme 12). 38 This RCEYM approach allows the synthesis of previously inaccessible selenium-containing bicyclic β-lactams.…”

Section: Scheme 7 Synthesis Of Selenating Reagent and Key Intermediatesmentioning

confidence: 99%

Selenium-Containing Bicyclic β-Lactams

Garud¹,

Ninomiya²,

Koketsu³

2010

HETEROCYCLES

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The first β-lactam ring system was synthesized by H. Staudinger in 1907, but β-lactams as a class of compounds became attractive only after it was established that penicillin contained a β-lactam unit as the structural feature. Over the years, countless numbers of penicillin derivatives and a variety of new β-lactam ring systems have been prepared, tested, and introduced. As a class of β-lactam derivatives, selenium-containing bicyclic β-lactams have received only a limited attention. In this review the advances in the development of synthesis methods for selenium-containing bicyclic β-lactams are presented and discussed.

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“…Later our efforts led to the synthesis of various kinds of Se-containing -lactams via iodocyclization (Scheme 22) [210] and ring-closure metathesis (Scheme 23) [211,212]. Recently, a review about Se-containing bicyclic -lactams was published by our group [213].…”

Section: Se-containing -Lactamsmentioning

confidence: 99%