Rhodium-Catalyzed Asymmetric Arylation of <i>N</i>-Tosyl Ketimines

Shintani, Ryo; Takeda, Masatoshi; Tsuji, Tetsuro; Hayashi, Tamio

doi:10.1021/ja106114q

Cited by 145 publications

(41 citation statements)

References 57 publications

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“…[126] Avery different chemocatalytic strategy towards optically active amines involves the addition of C-nucleophiles to imines.T his includes aw ide range of nucleophiles as demonstrated by Charette (alkyl nucleophiles), [127] Carreira (alkynes), [128] Aponick (alkynes), [129] Knochel (alkynes), [130] Shibasaki (allyl), [131] and Hayashi (allyl). [132] More recently,c hiral diarylmethylamines can be obtained through desymmetrization of prochiral diarylmethylamines,a sd emonstrated in pioneering work by Yu. [133] An additional strategy relies on the use of Pd-or Ircatalysts [134] to conduct enantioselective allylation reactions (cf.S ection 3.3).…”

Section: Reviewsmentioning

confidence: 99%

Enantioselective Chemo‐ and Biocatalysis: Partners in Retrosynthesis

et al. 2017

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Recent developments of stereoselective biocatalytic and chemocatalytic methods are discussed. The review provides a guide to the use of biocatalytic methods in the area of chemical synthesis with focused attention on retrosynthetic considerations and analysis. The transformations presented are organized according to bond disconnections and attendant synthetic methods. The review is expected to lead to better understanding of the characteristics and distinctions of the two complementary approaches. It depicts for researchers in bio- and chemocatalysis a road map of challenges and opportunities for the evolution (and at times revolution) in chemical synthesis.

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Section: Reviewsmentioning

confidence: 99%

Enantioselective Chemo‐ and Biocatalysis: Partners in Retrosynthesis

et al. 2017

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“…Shintani, Hayashi, et al reported the catalytic asymmetric arylation of acyclic N-sulfonyl ketimines through the use of Rh/chiral diene 65 catalysis. 41,42 For N-tosyl (N-Ts) ketimines, the reactions generally proceeded in a highly enantioselective manner at 60°C with sodium tetraarylborates 46 as arylating agents (Scheme 14). A drawback of this catalytic system was the sacrificial use of three aryl groups from 46.…”

Section: Acyclic or C=n Exocyclic Ketimines Without An α-Electron-witmentioning

confidence: 99%

Recent Advances in Catalytic Asymmetric C–C Bond-Forming Reactions to Ketimines Promoted by Metal-Based Catalysts

Kumagai

Shibasaki

2014

Bulletin of the Chemical Society of Japan

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Recent progress (post-2010) in the field of metal-catalyzed asymmetric CC bond-forming reactions using ketimines as electrophiles is reviewed. Compared with the corresponding aldimines, ketimines generally display less inherent reactivity and the two substituents on the imine carbon hamper prochiral-face-selection for enantioselective reactions. Recent advances with newly developed catalytic systems have resulted in several solutions to these long-standing problems. The construction of tetrasubstituted stereogenic centers is a crucial topic of asymmetric catalysis in the 21st century, and it is becoming increasingly clear that reactions using ketimines as electrophiles become one of the most important routes to access such chemical entities.

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“…[20,21] This latter method, developed by Ruano et al, is generally considered the most reliable method for the synthesis of N-sulfonyl ketimines. [13,14,[22][23][24] Although trustworthy, the method has some significant drawbacks. It involves the handling of peracids and peroxy compounds and is time consuming, since it requires several synthetic operations such as: 1) the preparation of the sulfinamide (only the chiral molecule is commercially available) 2) the condensation with the corresponding ketone, requiring 36 h of reflux, and finally 3) the oxidation of the N-sulfinyl imine with MCPBA.…”

Section: Introductionmentioning

confidence: 99%