Phosphine‐Catalyzed [4+2] Cycloadditions of Allenic Ketones: Enantioselective Synthesis of Functionalized Tetrahydropyridines

Wang, Xin; Lu, Mengxue; Su, Qin; Zhou, Minghui; Addepalli, Yesu; Yao, Weijun; Wang, Zhen; Lü, Yixin

doi:10.1002/asia.201901104

Cited by 20 publications

(4 citation statements)

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“…Optically pure phosphine 456 a has been employed as chiral organocatalyst, providing compounds 455 with enantioselectivities up to >99% (Scheme 78a) [211] . In a related approach, α‐allenones 2 in the presence of phosphine catalyst 456 b behave as C4 synthons, and therefore undergo formal [4+2] cycloaddition with imines 459 , generating alternative piperidine systems 460 (Scheme 78b) [212] . The above results show one more time the intriguing and divergent reactivity of allenones, depending on their substitution pattern and reaction conditions.…”

Section: Synthetic Utilitymentioning

confidence: 99%

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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Conjugated and non-conjugated allenones appear as recurring motifs in organic synthesis, natural products and mechanistic investigations showing unique properties and applications. The ability of allenones to build cycles has provided a direct access to strained systems, medium-sized rings, arenes, heterocycles and complex polycycles. In addition, allenones have served as models in mechanistic investigations and catalysis. The critic compilation herein presented will provide an exhaustive overview of the synthetic possibilities allenones may offer, which certainly will inspire our community in their search of more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and improve our knowledge in theoretical organic chemistry. Great part of this review will discuss synthetic aspects, catalysis innovation and mechanistic insights of the chemical transformations implying the allenone motif. In addition, many examples on total synthesis and pharmacologically active compounds will be described. We hope that this overview will be attractive to the organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products and medicinal chemistry communities. 3.5. Synthesis of Spirocycles and Bridged Structures 3.6. Open-Chain Structures from Allenones 3.7. Allenones in Total Synthesis 4.

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Section: Synthetic Utilitymentioning

confidence: 99%

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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“…Wang's group recently presented a chiral phosphine catalyzed [4+2] cycloaddition of α‐substituted allenic ketones as “C4 synthons” and N ‐sulfonyl cyclic ketimines. [ 76 ] Using amino‐acid‐ derived phosphine 140a developed by Lu's group, this asymmetric cycloaddition tolerates a wide range of α‐substituted allenic ketones and N ‐sulfonyl cyclic ketimines 227 , providing a series of chiral sultam‐fused tetrahydropyridines 228 bearing a quaternary stereocenter in high yields with good enantioselectivities (Scheme 59).…”

Section: Cycloaddition Reactions Catalyzed By Chiral Phosphinesmentioning

confidence: 99%

Asymmetric Reactions Catalyzed by Chiral Tertiary Phosphines

Wei

Shi

2020

Chin. J. Chem.

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Chiral tertiary phosphines are versatile Lewis base catalysts capable of promoting a wide range of asymmetric reactions. In particular, the recent designed chiral phosphines based on the concept of bi-/multifunctionality have been demonstrated to be effective catalysts for many types of asymmetric reactions such as (aza)-MBH reaction/RC reaction, cycloaddition reaction, domino reaction, nucleophilic addition reaction, etc. This review summarizes the recent advances in this field and highlights the selected significant achievements. Dr. Yin Wei (left) received her PhD from Ludwig-Maximilians-Universität in München (Germany) in 2009 under the direction of Professor Hendrik Zipse. Subsequently, she joined in Professor Min Shi's group at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (SIOC, CAS), and was promoted as an associate professor in 2012. She has authored over 100 scientific publications, and she is mainly working on the theoretical studies of organocatalysis.

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“…The catalytic asymmetric aza-Diels–Alder reaction is the most powerful method for constructing diverse tetrahydropyridine derivatives . To date, organo-catalyzed aza-[4+2] annulation of compounds such as chiral Brønsted acids, , chiral prolinol silyl ethers, , and chiral phosphines, metal-catalyzed dearomatization of pyridine, and C–H functionalization have been reported for the asymmetric synthesis of tetrahydropyridine derivatives.…”

mentioning

confidence: 99%