Rhodium‐Catalysed [4+2] Annulation of Aromatic Oximes with Terminal Alkenes by C−H/N−O Functionalization towards 3,4‐Dihydroisoquinolines

Zhang, Xu; Ouyang, Xuan‐Hui; Li, Yang; Chen, Bin; Li, Jin‐Heng

doi:10.1002/adsc.201900922

Cited by 11 publications

(6 citation statements)

References 41 publications

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“…[203] The above method was later improvised by Zhang et al by eliminating the need of additive to synthesize 3,4-dihydroisoquinolines 105 in good yields (Scheme 199). [204] Wang et al [205] Chu et al [206] and Lin et al [207] have developed a similar Rh-catalyzed annulation of benzylamines and diazo compounds. He et al have demonstrated Rh-catalyzed intramolecular reaction of bromonium ylides, which are obtained upon reaction of benzyl bromide 333 and αimino carbene to access 4-bromo-1,2-dihydroisoquinolines 334 (Scheme 201).…”

Section: Rh-catalyzed Isoquinoline Synthesismentioning

confidence: 99%

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Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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In the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N-heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.

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Section: Rh-catalyzed Isoquinoline Synthesismentioning

confidence: 99%

“…by eliminating the need of additive to synthesize 3,4‐dihydroisoquinolines 105 in good yields (Scheme 199). [204] …”

Section: Synthesis Of Isoquinoline Derivativesmentioning

confidence: 99%

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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“…[21][22][23] During the preparation of this manuscript, the group of Chen and Li reported the reaction of aromatic oximes with various styrenes to give dihydroisoquinoline heterocycles (Scheme 1, equation E). 24 However, similar reactions with aliphatic alkenes remained unexplored.…”

Section: Letter Syn Lettmentioning

confidence: 99%

Variability of Rhodium(III)-Catalyzed Reactions of Aromatic Oximes with Alkenes

Trifonova

Komarova

Chusov

et al. 2020

Synlett

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Acetophenone oxime reacts with various alkenes in the presence of the rhodium catalyst [Cp*RhCl2]2 (2.5 mol%; Cp* = pentamethylcyclopentadienyl) and 1,1,1,3,3,3-hexafluoropropan-2-ol as an important cosolvent. Styrene, aliphatic terminal alkenes, and strained cyclic alkenes gave the corresponding substituted dihydroisoquinolines in yields of 50–99%. On the other hand, alkenes containing functional groups close to the double bond gave a variety of different products. The reactions of acetophenone oxime with styrene or dec-1-ene in the presence of the chiral catalyst [(C5H2 t Bu2CH2 t Bu)RhI2]2 provided the corresponding dihydroisoquinolines with improved regioselectivity but a low enantiomeric ratio (61:39 in both cases).

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“…On the other hand, 3,4-dihydroisoquinolines (DHIQ) as an inactivated cyclic imine have been broadly applied as valuable synthons which could react with nucleophilic reagent to fulfill potential active tetrahydroisoquinoline derivatives in organic synthesis [69][70][71][72][73][74][75][76]. In 2017, the Cui and co-workers developed catalyst-free [3 + 2] cyclization of 3,4-dihydroisoquinolines and aldehydes-derived MBH carbonates to provide tetrahydropyrroloisoquinolines in good yields (Scheme 1a) [77].…”

Section: Introductionmentioning

confidence: 99%

Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines

Wang,

Zhou,

Jia

et al. 2023

Molecules

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Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita–Baylis–Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented synthesis of a series of novel and structurally complex spiro multi heterocyclic skeletons in good yields (up to 87% and 90%, respectively) with excellent diastereoselectivities (up to >25:1 dr). In particular, the switchable [4 + 2] and [3 + 2] annulation reactions are controlled by tuning the hydroxyl protecting group on the ninhydrin-derived MBH adduct to deliver structural diverse spiro[indene-2,2′-[1,3]oxazino[2,3-a]isoquinoline] and spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline], respectively. Furthermore, the relative configuration and chemical structure of two kinds of cycloadducts were confirmed through X-ray diffraction analysis.

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Rhodium‐Catalysed [4+2] Annulation of Aromatic Oximes with Terminal Alkenes by C−H/N−O Functionalization towards 3,4‐Dihydroisoquinolines

Cited by 11 publications

References 41 publications

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

Variability of Rhodium(III)-Catalyzed Reactions of Aromatic Oximes with Alkenes

Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines

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