Carbonylative [2+2] cycloaddition for the construction of β-lactam skeleton with palladium catalyst

Torii, Sigeru; Okumoto, Hiroshi; Sadakane, Masahiro; Hai, Abdul; Tanaka, Hideo

doi:10.1016/0040-4039(93)88102-o

Cited by 45 publications

(17 citation statements)

References 32 publications

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“…According to previously reported data, [33,34] as well as the data in Table 1, the CO insertion would always occur between the carbon (C-3) directly attached to the halogen and the palladium (structure 17). When the halogen is not in the terminal position of the allylic chain, we found, instead, that the insertion occurs at the less hindered carbon atom (C-1) of structure 15.…”

Section: Resultsmentioning

confidence: 84%

“…According to the mechanism proposed by Torii [33] (Scheme 6), the reaction starts by the formation of the π-allyl palladium complex 16. In the acyl complex 17, derived from the insertion of CO, the protons alpha to the carbonyl group show appreciable acidity.…”

Section: Resultsmentioning

confidence: 99%

“…Scheme 3 d) Palladium-catalyzed carbonylation of the allyl phosphate 4 in the presence of imines, under CO pressure. [33,34] The reaction is stereoselective since the formation of the trans-7 or the cis-8 β-lactam depends on the imine used for the coupling. An imine conjugated 6 with a carbonyl group gives the cis-β-lactam, whereas the unconjugated imine 5 gives the trans isomer (Scheme 4).…”

Section: Introductionmentioning

confidence: 99%

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The Stereoselective Synthesis of Alkenyl‐β‐lactams by Palladium‐Catalyzed [2+2] Carbonylative Cycloaddition

et al. 2004

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Allyl halides of different structures, under CO pressure, in the presence of Et3N, a catalytic amount of Pd(OAc)2, and triphenylphosphane as ligand, undergo a [2+2] cycloaddition reaction with various imines. The reaction is highly regio‐ and stereoselective: β‐lactams are formed in good yields and with trans diastereoselectivity in both the β‐lactam ring and the vinylic moiety. New and important information is suggested regarding the known reaction mechanism. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Stereoselective Synthesis of Alkenyl‐β‐lactams by Palladium‐Catalyzed [2+2] Carbonylative Cycloaddition

et al. 2004

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“…The palladium-catalyzed carbonylation reaction of allyl diethyl phosphate, in the presence of imines, gives either cis-or trans-3-vinyl-ˇ-lactams, in high yields and in a stereoselective fashion (equation 160) 574,575 . The reaction is a [2 C 2] cycloaddition process which occurs under simple and mild conditions and has significantly more potential than the reaction of imines with ketenes (due to the more forcing conditions that are usually required to form the ketene intermediates).…”

Section: Three-and Four-membered Ringsmentioning

confidence: 99%

Some Synthetic Uses of Double‐Bonded Functional Groups

Hoyle

2009

Patai's Chemistry of Functional Groups

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“…83 87 It appeared that the substituent on nitrogen atom of the imines influenced the stereoselectivity. The phenyl and the n-butyl groups led to cyclization toward the formation of the trans isomer.…”

Section: Alkene-isocyanate Cycloadditionsmentioning

confidence: 99%

Advances in synthesis of monocyclic beta-lactams

Singh¹,

Sudheesh²

2014

Arkivoc

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Recent years have witnessed significant advancement in cycloaddition and cyclization strategies for the synthesis of monocyclic β-lactams. Cycloadditions include the Staudinger's keteneimine cycloaddtions and related reaction. Cyclization reactions are reported to furnish β-lactams through N 1 -C 2 , N 1 -C 4 and C 3 -C 4 bond formations employing substrates like β-amino esters, β-amino alcohols, β-hydroxamate esters, and α-amino diazocarbonyls, etc. Some other strategies are silyl carbonylation reactions, ring-enlargement of aziridines, cleavage of one ring of a bicyclic β-lactam, and functional group transformations on the β-lactam rings. Recently, some multi-component reactions have also been designed. This article reviews the advances made in synthetic approaches to monocyclic β-lactams during last five years.

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Carbonylative [2+2] cycloaddition for the construction of β-lactam skeleton with palladium catalyst

Cited by 45 publications

References 32 publications

The Stereoselective Synthesis of Alkenyl‐β‐lactams by Palladium‐Catalyzed [2+2] Carbonylative Cycloaddition

The Stereoselective Synthesis of Alkenyl‐β‐lactams by Palladium‐Catalyzed [2+2] Carbonylative Cycloaddition

Some Synthetic Uses of Double‐Bonded Functional Groups

Advances in synthesis of monocyclic beta-lactams

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