Highly enantioselective hydroformylation of olefins catalyzed by new phosphine phosphite-rhodium(I) complexes

Sakai, Nozomu; Mano, Satoshi; Nozaki, Kyoko; Takaya, Hidemasa

doi:10.1021/ja00068a095

Cited by 465 publications

(180 citation statements)

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“…Esterases from yeasts are also gaining industrial interest with applications in laundry detergents and in dairy industries [23,24], while little attention has been paid to lipases from yeasts [7,25,26]. Although peptic enzymes for industrial uses have been so far pro duced by molds and bacteria [27], the pectinolytic activity of yeasts has, however, been studied with ambiguous results [28,29].…”

Section: Enzymatic Activitiesmentioning

confidence: 99%

Yeast Ecology of Fermented Table Olives: A Tool for Biotechnological Applications

Anagnostopoulos¹,

Bozoudi²,

Tsaltas³

2017

Yeast - Industrial Applications

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The table olive is considered to be a traditional fermented vegetable in the Mediter ranean countries and its production and consumption is recently spreading all around the world. The presence of yeasts is very important during olive fermentation due to their double role. On one hand, yeasts maintain desirable biochemical activities (lipase, esterase, β-glucosidase, catalase, production of killer factors, etc.) with essen tial technological applications in this fermented vegetable. On the other hand, spoil age activity may be shown. However, recent studies have reported that yeasts coming from table olives would be a new source of potential probiotics. Indeed, many yeast species found in table olive processing, have been reported to demonstrate such prop erties. Thus, starter cultures technology will play significant role, not only in olive fermentation by controlling the safety and the quality of the final product, but also in consumer's health.

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Section: Enzymatic Activitiesmentioning

confidence: 99%

Yeast Ecology of Fermented Table Olives: A Tool for Biotechnological Applications

Anagnostopoulos¹,

Bozoudi²,

Tsaltas³

2017

Yeast - Industrial Applications

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“…In 2003, after the discovery of (R,S)-Binaphos [29], a milestone ligand for asymmetric hydroformylation, Nozaki successfully anchored this ligand to a highly cross-linked polystyrene support [30] (Figure 6). Several organic-solvent-free asymmetric hydroformylations were performed.…”

Section: Catalyst Immobilized On a Solid Supportmentioning

confidence: 99%

Recent Advances in Continuous Rhodium-Catalyzed Hydroformylation

Wang¹

2015

J Flow Chem

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“…Only recently, the phosphino-phosphite ligand (R,S)-binaphos, introduced by Takaya and co-workers [13], and the largebite-angle diphosphites independently introduced by Babin and Whiteker [14] and van Leeuwen and co-workers [15] led to real breakthroughs.…”

Section: Dedicated To Professor Giambattista Consiglio On the Occasiomentioning

confidence: 99%

Chiral (Diphosphonite)platinum Complexes in Asymmetric Hydroformylation

Duren

Cornelissen

Vlugt

et al. 2006

Helvetica Chimica Acta

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Dedicated to Professor Giambattista Consiglio on the occasion of his 65th birthdayThe chiral diphosphonite ligand (11bR,11'bR)-4,4'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin] ((R,R)-XantBino; (R)-1), based on a rigid xanthene backbone, was applied in the Pt/Sn-catalyzed hydroformylation of styrene (4a), 4-methylstyrene (4b), vinyl acetate (4c), and allyl acetate (4d), by using a Pt/Sn ratio of 1 : 1. High ee of up to 80% were observed, along with good regioselectivities towards the desired branched aldehydes. For styrene, an interesting inversion in the stereoselection process was observed at elevated temperatures, and a mechanism is proposed considering the temperature dependence of the regioselectivity. Introduction. -The asymmetric hydroformylation of alkenes is a reaction of great potential for the production of optically active aldehydes, which are versatile building blocks in synthetic organic chemistry [1] [2]. Initial work on asymmetric hydroformylation in the presence of cobalt [3], platinum [4], and rhodium catalysts [5] resulted in very low enantioselectivities, but the Pt/Sn-catalyst, modified with chiral diphosphine ligands and pioneered by Consiglio and co-workers led to much better results than any previous system [6]. However, these catalysts showed poor regioselectivities, yielding the branched, chiral aldehydes in only 50 -70% and in some cases of up to 80% [7]. Additionally, the formation of hydrogenated products and double-bond isomerization as unwanted side reactions were observed.Typically, a large excess of up to 6 equiv. of SnCl 2 was necessary to form stable catalysts and to avoid decomposition to Pt-black. However, this excess causes significant product racemization, as observed problem for the early systems, leading to lower overall enantioselectivities [6]. To overcome these drawbacks, trapping agents, e.g., triethyl orthoformate (HC(OEt) 3 ) were added, to achieve in situ protection of the aldehyde and to reach high enantioselectivities of up to 96% [8] [9]. Alternatively, preformation of the Pt/Sn bimetallic catalyst species resulted in higher enantioselectivities as well as chemo-and regioselectivities [10] [11].

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Highly enantioselective hydroformylation of olefins catalyzed by new phosphine phosphite-rhodium(I) complexes

Cited by 465 publications

References 0 publications

Yeast Ecology of Fermented Table Olives: A Tool for Biotechnological Applications

Yeast Ecology of Fermented Table Olives: A Tool for Biotechnological Applications

Recent Advances in Continuous Rhodium-Catalyzed Hydroformylation

Chiral (Diphosphonite)platinum Complexes in Asymmetric Hydroformylation

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