Enantioselective Rauhut–Currier‐Type 1,6‐Conjugate Addition of Methyl Vinyl Ketone to <i>para</i>‐Quinone Methides

Kang, Tian-Chen; Wu, Lu-Ping; Yu, Qi-Wen; Wu, Xin‐Yan

doi:10.1002/chem.201700520

Cited by 55 publications

(16 citation statements)

References 80 publications

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“…In 2017, Wu and co-workers reported a nucleophilic phosphine-catalyzed RC-type 1,6-conjugate addition of methyl vinyl ketone to p -QMs (Scheme 44). 129 Using 10 mol % of the phosphine P15 as the chiral catalyst and dichloromethane as the solvent at −20 °C, the asymmetric RC-type 1,6-conjugate additions of p -QMs presenting various substituents and MVK provided their products in excellent yields (91–99%) with excellent enantioselectivities (92–98% ee).…”

Section: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

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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Section: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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“…Chiral BINOL‐derived tertiary phosphine C1 [12] could afford the desired product 4 a but without enantiocontrol (Table 1, entry 5), and a bifunctional catalyst C2 [13] with a thiourea moiety gave better results (Table 1, entry 6). In addition, good enantioselectivity was achieved with L ‐phenylglycine derived phosphine C3 [14] (Table 1, entry 7), and high levels of stereoselectivity could be obtained when C4 or C5 with a bulkier substituent was employed (Table 1, entries 8 and 9). Catalyst C6 with an N ‐tosyl group was tested as well, but provided inferior results (Table 1, entry 10).…”

Section: Methodsmentioning

confidence: 99%

Phosphine Catalyzed Enantioselective Cascade Reaction Initiated by Intermolecular Cross Rauhut‐Currier Reaction of Electron‐Deficientortho‐Formyl Styrenes

et al. 2020

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The Rauhut‐Currier reaction generally employs α,β‐unsaturated carbonyl compounds and nitroalkenes as the substrates. Here we develop an enantioselective formal [4+2] annulation reaction, which is initiated by an intermolecular cross Rauhut‐Currier reaction between electron‐deficient ortho‐formyl‐styrenes and 2‐benzoyl‐acrylonitriles catalyzed by an L‐phenylglycine‐derived phosphine, followed by a cascade aldol/acyl transfer/elimination process. A series of enantioenriched dialin frameworks with an unusual exo‐double bond are furnished in fair to good yields with moderate to excellent enantioselectivity, and the architectures with higher molecular complexity can be constructed via simple transformations.

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“…Similarly,W ua nd co-workers reported an enantioselective Rauhut-Currier reactionb etween p-QMs 64 and methyl vinyl ketone (65), catalyzed by chiral cyclohexane-based phosphineamide catalyst C18 (Scheme 20). [25] The nucleophilic phosphine, which contained as ingle Brønsted acid group, only activated the methylv inyl ketone through nucleophilic attack and ah ydrogen-bonding interaction, whereas the electrophilic p-QM could also be activated by aH -bonding interaction with the second Brønsted acid group of the multifunctional catalyst. With ac atalyst loading of 10 mol %, the Rauhut-Currier reaction proceeded promptly and 1,6-adducts 66 wereo btained in excellent yields andw ith excellent enantioselectivities.…”

Section: Chiralamide-phosphinesmentioning

confidence: 99%

Recent Advances in the Catalytic Enantioselective Reactions of para‐Quinone Methides

Zhang

et al. 2018

Chemistry An Asian Journal

180

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In recent years, the catalytic enantioselective reactions of p-QMs have drawn much attention, because of their distinctive reactivities. As such, a variety of chiral catalytic systems have been developed. This Focus Review describes the reactions of p-QMs according to the chiral catalyst system used, with the aim of provide the first complete picture of the exciting developments in this field. Special emphasis is placed on recent work regarding their reaction mechanisms.

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Enantioselective Rauhut–Currier‐Type 1,6‐Conjugate Addition of Methyl Vinyl Ketone to para‐Quinone Methides

Cited by 55 publications

References 80 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

Phosphine Catalyzed Enantioselective Cascade Reaction Initiated by Intermolecular Cross Rauhut‐Currier Reaction of Electron‐Deficientortho‐Formyl Styrenes

Recent Advances in the Catalytic Enantioselective Reactions of para‐Quinone Methides

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