Stereoselective synthesis of 4-substituted-cyclic sulfamidate-5-carboxylates by asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution and applications to concise stereoselective syntheses of (−)-epi-cytoxazone and the taxotere side-chain

Kim, Jinah; Seo, Yeon Ji; Kang, Sun Hyung; Han, Jae Woo; Lee, Hyeon‐Kyu

doi:10.1039/c4cc06395c

Cited by 30 publications

(19 citation statements)

References 44 publications

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“…An example with cyclohexyl was less selective (Figure 23). [93] The application could be extended efficiently to 5-phosphonate-containing substrates. In some cases both the de and e.e.…”

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confidence: 99%

Imino Transfer Hydrogenation Reductions

Wills

2016

Top Curr Chem (Z)

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This review contains a summary of recent developments in the transfer hydrogenation of C=N bonds, with a particularly focus on reports from within the last 10 years and asymmetric transformations. However, earlier work in the area is also discussed in order to provide context for the more recent results described. I focus strongly on the Ru/TsDPEN class of asymmetric transfer hydrogenation reactions originally reported by Noyori et al., together with examples of their applications, particularly to medically valuable target molecules. The recent developments in the area of highly active imine-reduction catalysts, notably those based on iridium, are also described in some detail. I discuss diastereoselective reduction methods as a route to the synthesis of chiral amines using transfer hydrogenation. The recent development of a methodology for positioning reduction complexes within chiral proteins, permitting the generation of asymmetric reduction products through a directed modification of the protein environment in a controlled manner, is also discussed.

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“…An example with cyclohexyl was less selective (Figure 23). [93] The application could be extended efficiently to 5-phosphonate-containing substrates. In some cases both the de and e.e.…”

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confidence: 99%

Imino Transfer Hydrogenation Reductions

Wills

2016

Top Curr Chem (Z)

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“…Several substituted sulfamidates have been reduced under these conditions with excellent yields (54-99%) and stereoselectivity (only cis product, up to 99% ee) (Scheme 48). 73 It should be pointed out that several substrates bearing alkyl substituents have also been reduced with moderate to high levels of stereoselectivity. The authors observed that changing the HCO 2 H/Et 3 N ratio from 5:2 to 1:1 had a significant positive effect on both the reactivity and the stereochemical outcome of the reaction.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

et al. 2016

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The transition-metal-catalyzed asymmetric transfer hydrogenation (ATH) and asymmetric hydrogenation (AH) of α-and β-substituted ketone or imine derivatives are efficient methods for accessing chiral alcohols or amines bearing up to three stereogenic centers through a dynamic kinetic resolution (DKR) process. This review provides a summary of recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of substrates. Conclusion

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“…A variant of the methodology shown in Scheme was applied to the ester derivatives 70 , which under the same reaction conditions and with the same catalyst afforded the expected products 71 with excellent results (Scheme ) …”

Section: Reaction Scope: Metal Catalysts and Chiral Ligandsmentioning

confidence: 99%

Catalytic Asymmetric Transfer Hydrogenation of Imines: Recent Advances

Foubelo

Yus

2015

The Chemical Record

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Abstract:In this review article recent developments in the asymmetric transfer hydrogenation of imines from 2008 up today are presented. The main methodology involves either metalcatalyzed procedures in the presence of a chiral ligand or organocatalyzed technologies using a Hantzsch ester and a chiral BINOL-derived phosphoric acid. The most important procedures are collected paying special attention to the synthetic application of this methodology in synthetic organic chemistry.

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Stereoselective synthesis of 4-substituted-cyclic sulfamidate-5-carboxylates by asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution and applications to concise stereoselective syntheses of (−)-epi-cytoxazone and the taxotere side-chain

Abstract: Dynamic kinetic resolution driven, asymmetric transfer hydrogenation reactions of cyclic sulfamidate imine-5-carboxylate esters were developed. Applications of the new methodology to stereoselective syntheses of the taxotere side-chain and (-)-epi-cytoxazone are described.

Cited by 30 publications

References 44 publications

Imino Transfer Hydrogenation Reductions

Imino Transfer Hydrogenation Reductions

Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

Catalytic Asymmetric Transfer Hydrogenation of Imines: Recent Advances

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