Multicomponent Diene‐Transmissive Diels–Alder Sequences Featuring Aminodendralenes

Tan, Siu Min; Willis, Anthony C.; Paddon‐Row, Michael N.; Sherburn, Michael S.

doi:10.1002/anie.201510925

Cited by 26 publications

(8 citation statements)

References 48 publications

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“…23 Very recently, Sherburn's group has also synthesized amino dendralenes via condensation of a dienal and an amine (1° or 2°) (Scheme 3). 24 Most of these methods yielded unsubstituted or scantly substituted dendralenes. Only a handful of procedures have been reported in the literature regarding the synthesis of dendralenes with multiple substituents.…”

Section: Scheme 2 Early Methods For the Synthesis Of [3]dendralenementioning

confidence: 99%

[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds

Ghosh

Naidu

Singh

2017

Synlett

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[3]Dendralenes are exquisite molecules as they exhibit enormous potential for the rapid generation of architecturally esoteric scaffolds when subjected to tandem Diels–Alder reactions, but their synthesis is a tall order. In conjunction with diversity-oriented synthesis, [3]dendralenes satisfy the potential demand for simultaneous and efficient synthesis of intricate collections of molecules that exhibit a range of activities for lead generation in drug discovery. This account chronicles our roller-coaster journey and systematic approach beginning from the synthesis of extremely unstable, non-isolable [3]dendralenes through moderately stable examples and then finally, highly functionalized, stable [3]dendralenes via sequential methylenation (using dimethylsulfonium methylide) and Horner–Wadsworth–Emmons olefination. It also describes the study of the attributes affecting their stability and reactivity with various dienophiles. In addition, it reports on how these dendralenes, upon astute maneuvering, can be engaged in a diene-transmissive Diels–Alder (DTDA) sequence, thus harnessing their full potential by construction of a small but diverse library of complex frameworks in a quick and efficient manner, with step and atom economy.1 Introduction2 Literature Methods for [3]Dendralene Synthesis3 Our Tryst with [3]Dendralenes3.1 Serendipitous Olefination with the Corey–Chaykovsky Ylide3.2 Synthesis of [3]Dendralenes and Reactivity/Stability Studies3.3 Diels–Alder Reactions of [3]Dendralenes3.4 Tuning of [3]Dendralenes for the DTDA Reactions3.5 Diversity-Oriented Synthesis with [3]Dendralenes3.6 Rationalization of Factors Governing the Stability and Reactivity of [3]Dendralenes4 Conclusions

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Section: Scheme 2 Early Methods For the Synthesis Of [3]dendralenementioning

confidence: 99%

[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds

Ghosh

Naidu

Singh

2017

Synlett

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“…reaction with pyrrolidine 3a, different substituted α,βunsaturated aldehydes and only nitrostyrenes as dienophiles (Scheme 2a). In contrast, the group of Sherburn 7 introduce different dienophiles, morpholine, but just working with one aldehyde 5 which is a very reactive aldehyde obtaining high to excellent yields (Scheme 2b). In this work only one example with benzylamine was reported.…”

Section: A R T I C L E I N F O Abstract M a N U S C R I P T A mentioning

confidence: 99%

“…4.2.2. (3aS*,4R*,4,7,3(2H)-dione (6b): yellow prisms (52.8 mg, 61% yield), mp 75-77 °C. IR (neat) ߥ max : 1684,1475,1428,1399,1344,1173,1145,1071,915,741, 699 cm -1 .…”

Section: General Procedures For the Synthesis Of Productsmentioning

confidence: 99%

“…4 Hz,CCHCHCF),133.9,139.8 (ArC) 4.2.4. (3aS*,4R*,7S*,4,7,: brown sticky oil (43.5 mg, 50% yield). IR (neat) ߥ max : 1704,1598,1498,1455,1383,1266,1179,733, 695 cm -1 .…”

Section: 23mentioning

confidence: 99%

“…MS (EI) m/z: 346 (M + , 7%), 345 (26), 255 (32), 241 12 4.2.6. (3aS*,4R*,4,7,3(2H)-dione (6f): brown sticky oil (36.0 mg, 40% yield). IR (neat) ߥ max : 1692,1431,1399,1344,1181,1160,910,729, 699 cm -1 .…”

Section: 25mentioning

confidence: 99%

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Diastereoselective multicomponent Amine-Aldehyde-Dienophile (AAD) process for the synthesis of polysubstituted cyclohex-2-enylamines

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The multicomponent Amine-Aldehyde-Dienophile reaction is optimized employing benzyl or 4methoxybenzylamine. The interest of the transformation consist in synthesis of polysubstituted cyclohex-2-enylamines. The study of the scope of this AAD process is carried out as well as the diastereoselective version employing commercially available chiral benzylic amines and a maleimide with the chiral information at the N-substituent. VCD spectroscopy is a very useful tool for the determination of the absolute configuration of the isolated enantiomerically enriched compounds.

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Bifunctional Ligand Enables Efficient Gold‐Catalyzed Hydroalkenylation of Propargylic Alcohol

et al. 2018

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Using the previously designed biphenyl-2-ylphosphine ligand, featuring aremote tertiary amino group,the first gold-catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields.Arange of alkenyltrifluoroborates are allowed as the alkenyl donor,a nd no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as ag eneral-base catalyst for promoting this novel gold catalysis with good efficiency.

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Multicomponent Diene‐Transmissive Diels–Alder Sequences Featuring Aminodendralenes

Cited by 26 publications

References 48 publications

[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds

[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds

Diastereoselective multicomponent Amine-Aldehyde-Dienophile (AAD) process for the synthesis of polysubstituted cyclohex-2-enylamines

Bifunctional Ligand Enables Efficient Gold‐Catalyzed Hydroalkenylation of Propargylic Alcohol

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