Phosphine‐Catalyzed Intramolecular Formal [3+2] Cycloaddition for Highly Diastereoselective Synthesis of Bicyclo[<i>n</i>.3.0] Compounds

Ye, Long‐Wu; Sun, Xiu‐Li; Wang, Qinggang; Tang, Yong

doi:10.1002/anie.200701460

Cited by 135 publications

(30 citation statements)

References 76 publications

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“…13 Interestingly, we isolated the allenoate 1a in the highest yield (56%) when using dimethyl sulfide as the catalyst in MeCN. 14 Dimethyl sulfide failed to provide any desired rearrangement products from any of our other tested substrates. The DABCO-mediated reaction was tolerant of various alkyl groups, providing the desired products in modest yields.…”

mentioning

confidence: 78%

Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

Andrews¹,

Blank²,

Kwon³

2012

Chem. Commun.

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An array of N-tosylated α-aminoalkylallenic esters was prepared and their cyclization under the influence of nucleophilic phosphine catalysts was explored. The α-aminoalkylallenic esters were prepared through aza-Baylis–Hillman reactions or novel DABCO-mediated decarboxylative rearrangements of allenylic carbamates. Conversion of these substrates to 3-carbethoxy-2-alkyl-3-pyrrolines was facilitated through Ph3P-catalyzed intramolecular γ-umpolung addition.

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mentioning

confidence: 78%

Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

Andrews¹,

Blank²,

Kwon³

2012

Chem. Commun.

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“…Tang and co-workers [11] reported the first phosphane-catalyzed intramolecular ylide [3 + 2] annulations in 2007. In the presence of 20 mol-% PPh 3 and 1.5 equiv.…”

Section: Intramolecular [3 + 2] Annulationsmentioning

confidence: 99%

Advances in Annulation Reactions Initiated by Phosphorus Ylides Generated in situ

Zhou

2016

Eur J Org Chem

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Over the past two decades, the rapid development of nucleophilic phosphane catalysis has transported phosphorus ylide chemistry into an area beyond olefination. Phosphorus ylides generated in situ on nucleophilic addition of phosphanes to electrophilic unsaturated species, followed by some necessary proton-transfer steps, have effected many powerful annulation reactions to construct carbo-and heterocycles

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“…63 Bicyclic ring structures are formed in good yields and with good diastereoselectivities (Scheme 72). …”

Section: Phosphine Catalysis Of Morita–baylis–hillman Alcohol Derimentioning

confidence: 99%

Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs

2013

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In nucleophilic phosphine catalysis, tertiary phosphines undergo conjugate additions to activated carbon–carbon multiple bonds to form β-phosphonium enolates, β-phosphonium dienolates, β-phosphonium enoates, and vinyl phosphonium ylides as intermediates. When these reactive zwitterionic species react with nucleophiles and electrophiles, they may generate carbo- and heterocycles with multifarious molecular architectures. This Article describes the reactivities of these phosphonium zwitterions, the applications of phosphine catalysis in the syntheses of biologically active compounds and natural products, and recent developments in the enantioselective phosphine catalysis.

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Phosphine‐Catalyzed Intramolecular Formal [3+2] Cycloaddition for Highly Diastereoselective Synthesis of Bicyclo[n.3.0] Compounds

Cited by 135 publications

References 76 publications

Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

Advances in Annulation Reactions Initiated by Phosphorus Ylides Generated in situ

Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs

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