Asymmetric transfer hydrogenation of ketones and imines with novel water-soluble chiral diamine as ligand in neat water

Li, Li; Wu, Jiashou; Wang, Fei; Liao, Jian; Zhang, Hua; Lian, Chunxia; Zhu, Jin; Deng, Jingen

doi:10.1039/b611809g

Cited by 101 publications

(48 citation statements)

References 18 publications

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“…Two other reports on the asymmetric transfer hydrogenation of imines in water appeared in 2007. Zhu and coworkers reported an amine-functionalized relative of 26 that could be used for the rhodium-catalyzed reaction [179], and Canivet and S€ uss-Fink synthesized a variety of [(amine-amido)(arene)RuOH 2 ] þ [BF 4 ] À salts as catalysts for the reaction [180]. Both used HCO 2 Na as the hydrogen source.…”

Section: Reducing the Environmental Impact Of The Reactionmentioning

confidence: 99%

Chiral Amines from Transition‐Metal‐Mediated Hydrogenation and Transfer Hydrogenation

Church¹,

Andersson²

2010

Chiral Amine Synthesis

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This chapter focuses specifically on the synthesis of amines of the form HNR Ã R 1 , NR Ã R 1 R 2 , and HN(X)R Ã (R Ã ¼ chiral alkyl group; R 1 , R 2 ¼ alkyl or aryl groups; X ¼ heteroatom such as N, S, or P) via the asymmetric hydrogenation of imines, enamines, and iminiums. Thus, we will discuss the formation of amines that have (i) chirality a to the nitrogen, and (ii) no carbonyl group a to nitrogen. Many reported examples of this reaction use substrates with C¼N moieties in a ring, so cyclic amines will receive considerable attention. We will discuss in detail the formation of chiral amines using the asymmetric reduction of aza-aromatic substrates, which has been a popular topic in recent years, and will cover the use of N-carbonyl groups to facilitate this reaction. However, the hydrogenations of nonaromatic a,b-unsaturated amides will not be discussed. Though chiral amides (HN(R Ã )C(O)R 1 ) can be produced highly enantioselectively using these reactions, the sheer number of publications on the topic places it outside the scope of this chapter. These hydrogenations are, however, well covered in a number of existing books and review articles [1]. In addition, we will not cover the related process, reductive amination, which is discussed elsewhere in this book.6.2 Chiral Amines with a Disubstituted Nitrogen Atom, HNR Ã R 1 Direct Asymmetric Hydrogenation of Alkyl-and Aryl-Substituted IminesThough less developed than the analogous reductions of olefins and ketones, the iridium-catalyzed asymmetric hydrogenation of imines (especially N-benzyl and Naryl amines) has received considerable study. It has therefore been the subject of

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Section: Reducing the Environmental Impact Of The Reactionmentioning

confidence: 99%

Chiral Amines from Transition‐Metal‐Mediated Hydrogenation and Transfer Hydrogenation

Church¹,

Andersson²

2010

Chiral Amine Synthesis

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“…ATH of ketones was frequently performed using 2-propanol and formic acid/triethylamine azeotrope as the solvent as well as hydrogen source. Because water is a safe, inexpensive and environmentally friendly medium, catalytic asymmetric transfer hydrogenation of prochiral ketones in water has been energetically investigated [7][8][9][10][11][12]. ATH of ketones using the supported chiral catalysts has been of great interest due to several advantages, such as simplification of product workup, separation, isolation, and reuse of the catalyst [13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of polyethylene glycol supported chiral monosulfonamide and its application in asymmetric transfer hydrogenation of prochiral ketones

Zhou

Sun

2010

Reac Kinet Mech Cat

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A new polyethylene glycol supported chiral monosulfonamide was conveniently synthesized from (R,R)-1,2-diphenylethylenediamine. The ruthenium catalyst prepared from polyethylene glycol supported chiral monosulfonamide with [RuCl 2 (p-cymene)] 2 was used in the asymmetric transfer hydrogenation of prochiral ketones in neat water with good to excellent conversions and enantioselectivities. The catalyst could be easily recovered and reused several times.

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“…Asymmetric transfer hydrogenation (ATH) of prochiral ketones to enantiomerically pure secondary alcohols provides an attractive alternative to asymmetric hydrogenation due to its operational simplicity, the easy availability of hydrogen sources, lower cost, and safety [1][2][3][4][5][6][7][8] genation of ketones [9][10][11][12]. To date, many modified TsDPEN ligands have been developed and applied to this reaction, providing good conversion rates and enantioselectivities [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27]. Monosulfonamidecyclohexane-1,2-diamine [28,29], amino alcohols [30], and amino amides [31][32][33][34][35][36] have been found to be efficient ligands for the asymmetric transfer hydrogenation of ketones, too.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel chiral Schiff bases and their application in asymmetric transfer hydrogenation of prochiral ketones

Zhou

Bian

2008

Heteroatom Chemistry

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Asymmetric transfer hydrogenation of ketones and imines with novel water-soluble chiral diamine as ligand in neat water

Cited by 101 publications

References 18 publications

Chiral Amines from Transition‐Metal‐Mediated Hydrogenation and Transfer Hydrogenation

Chiral Amines from Transition‐Metal‐Mediated Hydrogenation and Transfer Hydrogenation

Synthesis of polyethylene glycol supported chiral monosulfonamide and its application in asymmetric transfer hydrogenation of prochiral ketones

Synthesis of novel chiral Schiff bases and their application in asymmetric transfer hydrogenation of prochiral ketones

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