Phosphine-catalyzed sequential annulation domino reaction: rapid construction of bicyclo[4.1.0]heptene skeletons

Zheng, Jie; Huang, You; Li, Zhengming

doi:10.1039/c4cc01097c

Cited by 38 publications

(8 citation statements)

References 67 publications

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“…[28] Mechanistically, the authors believed that the allylic phosphorus ylides 2, formed in situ from carbonates 1 and phosphanes, undergo sterically favored γ-addition to dienic sulfones 87 to give intermediates 89, which undergo intramolecular umpolung addition to generate intermediates 90. Proton transfer, followed by intramolecular substitution, furnishes the bicyclo[4.1.0]heptene products 88 and regenerates the phosphane catalyst.…”

Section: Cyclo[410]heptenes (Scheme 35)mentioning

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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Section: Cyclo[410]heptenes (Scheme 35)mentioning

confidence: 99%

Advances in Annulation Reactions Initiated by Phosphorus Ylides Generated in situ

Zhou

2016

Eur J Org Chem

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“…In 2014, another novel synthetic strategy was disclosed by the Huang group, further demonstrating the versatility of 1,3-bis(sulfonyl)butadienes in the preparation of functionalized bicyclo[4.1.0]heptenes (Scheme 589). 653 Under phosphine catalysis, the zwitterion 376 is generated from the MBHAD. Nucleophilic addition between the diene and the zwitterion 376 produces the intermediate 377 .…”

Section: Nucleophilic Phosphine Catalysis Of Mbh-alcohol Derivatives mentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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“…On the basis of the above results and the related literature precedent, a plausible mechanism for the DMAP‐catalyzed [4+2] benzannulation reaction between γ‐substituted allenoates with dienic sulfone derivatives is proposed in Scheme . The reaction was triggered by nucleophilic addition of DMAP to allenoate 2 a .…”

Section: Methodsmentioning

confidence: 76%

One‐Pot Synthesis of Polysubstituted Benzenes through a N,N‐dimethyl‐4‐aminopyridine (DMAP)‐Catalyzed [4+2] Benzannulation of 1,3‐Bis(sulfonyl)butadienes and γ‐Substituted Allenoates

Chang

Zheng

et al. 2016

Chemistry An Asian Journal

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A new strategy for the one-pot synthesis of polysubstituted benzenes through a N,N-dimethyl-4-aminopyridine (DMAP)-catalyzed [4+2] benzannulation from readily prepared 1,3-bis(sulfonyl)butadienes and γ-substituted allenoates is described. This method provides a facile, metal-free and general route to highly substituted benzenes under mild conditions in moderate-to-good yields with complete regioselectivity.

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Phosphine-catalyzed sequential annulation domino reaction: rapid construction of bicyclo[4.1.0]heptene skeletons

Cited by 38 publications

References 67 publications

Advances in Annulation Reactions Initiated by Phosphorus Ylides Generated in situ

Advances in Annulation Reactions Initiated by Phosphorus Ylides Generated in situ

Phosphine Organocatalysis

One‐Pot Synthesis of Polysubstituted Benzenes through a N,N‐dimethyl‐4‐aminopyridine (DMAP)‐Catalyzed [4+2] Benzannulation of 1,3‐Bis(sulfonyl)butadienes and γ‐Substituted Allenoates

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