Rhodium‐Catalyzed Asymmetric [2+2+2] Cycloaddition Reactions of 1,6‐Enynes and Oxabenzonorbornadienes

Ni, Jianxiao; Chen, Jingchao; Zhou, Yong‐Gui; Wang, Gaowei; Li, Sida; He, Zhenxiu; Sun, Weiqing; Fan, Baomin

doi:10.1002/adsc.201900380

Cited by 18 publications

(9 citation statements)

References 33 publications

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“…In 2019, Fan, Zhou, and co-workers established the Rhcatalyzed asymmetric [2+2+2] cycloaddition of 1,6-enynes and oxabenzonorbornadienes to access polycyclic compounds in 12-66% yield and 60-99% ee (Scheme 35). 97 The reaction was carried out in the presence of [Rh(cod) 2 ]BF 4 (0.5 mol%) as the rhodium precursor and (R)-Xyl-P-Phos as a ligand in 1,4-dioxane at 40 °C, and delivered a range of polycyclic cycloadducts bearing quaternary stereocenters. 1,6-Enynes having a nitrogen-or oxygen-tether were well tolerated whereas reactions with a carbon-linked 1,6-enyne or 1,7-enyne failed to afford the expected cycloadducts, and the use of internal alkynes and alkenes led to lower yields.…”

Section: Scheme 34mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.1 Introduction2 Formation of Carbocycles2.1 Intermolecular Reactions2.1.1 Cyclotrimerization of Alkynes2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.1 Cycloaddition of Alkynes with Nitriles3.2 Cycloaddition of 1,6-Diynes with Cyanamides3.3 Cycloaddition of 1,6-Diynes with Selenocyanates3.4 Cycloaddition of Imines with Allenes or Alkenes3.5 Cycloaddition of (Thio)Cyanates and Isocyanates3.6 Cycloaddition of 1,3,5-Triazines with Allenes3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion

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Section: Scheme 34mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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“…Recently, we have demonstrated the first example of asymmetric [2+2+2] cycloaddition reactions of 1,6‐enynes 95 with oxabenzonorbornadienes . The reaction proceeded under the catalytic system of [Rh(cod) 2 ]BF 4 and ( R )‐Xyl‐P‐Phos, affording various polycyclic products 96 with quaternary carbon centers in excellent enantioselectivities [Eq.…”

Section: Cycloaddition Reactions Of Norbornadienes With Alkynesmentioning

confidence: 99%

“…The reaction between these substrates also provided a convenient synthetic route to benzocoumarin derivatives which are electron‐transporting emitters . The synthetic application of the reaction between these two substrates was again demonstrated in the synthesis of 3a,9b‐dihydrobenzo[ g ]indoles which were further converted to benzo[ g ]indoles . The naphthofuran skeleton which is found in various natural products was successfully synthesized from these substrates .…”

Section: Synthetic Applications Of Reactions Between Norbornadienes Amentioning

confidence: 99%

Versatile Catalytic Reactions of Norbornadiene Derivatives with Alkynes

2020

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“…12 Following this, our group developed the first Rh-catalyzed asymmetric [2 + 2 + 2] cycloaddition reaction of a wide range of 1,6-enynes with oxabicyclic alkenes which afforded various polycyclic products that contain asymmetric quaternary carbon centers with excellent enantioselectivity. 13 We have also reported an efficient cobalt-catalyzed reaction of 1,6-enynes and thiols for the synthesis of different carbocyclic organosulfur compounds based on the ligands used. 14 Chalcones which consist of an enone carbonyl group are important frameworks with significant biological activities such as anticancer, anti-HIV, anti-inflammatory, etc.…”

Section: Introductionmentioning

confidence: 99%