Asymmetric Syntheses

Noyori, Ryoji; Hashiguchi, Shohei; Yamano, Toru

doi:10.1002/9783527618231.ch2i

Cited by 4 publications

References 154 publications

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Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Ager¹

2006

The Handbook of Homogeneous Hydrogenation

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23Enantioselective Alkene Hydrogenation: Introduction and Historic Overview Development of CAMP and DIPAMPDuring the late 1960s, Horner et al. [13] and Knowles and Sabacky [14] independently found that a chiral monodentate tertiary phosphine, in the presence of a rhodium complex, could provide enantioselective induction for a hydrogenation, although the amount of induction was small [15][16][17][18][19][20]. The chiral phosphine ligand replaced the triphenylphosphine in a Wilkinson-type catalyst [10,21,22]. At about this time, it was also found that [Rh(COD) 2 ] + or [Rh(NBD) 2 ] + could be used as catalyst precursors, without the need to perform ligand exchange reactions [23].Knowles found that the monophosphine CAMP (1a) could provide an ee-value of up to 88% for the reduction of dehydroamino acids. CAMP was an extension of PAMP (1b) that provides ee-values of 50-60% in analogous reactions [24]. At this time, Kagan showed that DIOP (2) (vide infra), where the stereogenic centers are not at phosphorus, could also provide enantioselective induction in an hydrogenation. DIOP also showed that a bisphosphine need not have the chirality at phosphorus, and that good stereoselectivity might result from a C 2 -symmetric ligand. Knowles then developed the C 2 -symmetric ligand DIPAMP (3) [22,25]. The use of Rh-DIPAMP for the synthesis of l-Dopa is well known and is still practiced today [12,22,27]. A number of variations of the DIPAMP structure were investigated for the synthesis of this important pharmaceutical, but the parent remains the best ligand in this class [22].

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Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Ager¹

2006

The Handbook of Homogeneous Hydrogenation

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Fakten sind der Feind der Wahrheit – Betrachtungen über Zufallsentdeckungen und ungeahnte Entwicklungen der asymmetrischen Katalyse

Noyori

2012

Angewandte Chemie

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“Der Zufall begünstigt nur den vorbereiteten Geist”, sagte Louis Pasteur. Zufallsereignisse, die dem Weg der Wissenschaft eine neue Richtung geben, geschehen oft infolge von Handlungen passionierter Individuen mit unverwechselbarem kulturellen und erzieherischen Hintergrund, einem ursprünglichen Wertempfinden und festen Prinzipien. Wissenschaft ist die Quelle menschlichen Wissens und besitzt einen unverzichtbaren kulturellen Wert. Wissenschaftsbasierte Technologien und die aus ihnen abgeleiteten Innovationen sind die Grundlage der zivilisierten Gesellschaft, in der wir heute leben. Alle wissenschaftlichen Bestrebungen beginnen mit Beobachtungen oder Fakten. Das eigentliche Ziel der Forschungsaktivität ist es aber, das gesammelte Wissen in etwas umzuwandeln, das neuen technologischen, ökonomischen oder sozialen Wert hat. Innovation ist ein entscheidender Aspekt, der den Fortbestand der Menschheit gewährleistet. Und wie die 50 Jahre meiner Forschung zeigen, wird das Umwandeln von Fakten in Werte durch den Dialog erleichtert. Wissenschaftler können die notwendige Gesamterfahrung nur erwerben, wenn sie in laufendem Gespräch mit den Gesellschaften, in deren Dienst sie stehen, sowie mit ihren Kollegen in anderen Nationen bleiben.

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Facts are the Enemy of Truth—Reflections on Serendipitous Discovery and Unforeseen Developments in Asymmetric Catalysis

Noyori

2012

Angew Chem Int Ed

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As Louis Pasteur said, "Chance favors only a prepared mind." Serendipitous events reorienting the pathway of science often occur through the actions of dedicated individuals with unique cultural and educational backgrounds, an original sense of values, and firm principles. Science is the fountainhead of human knowledge and possesses an indispensable cultural value. Science-based technologies and the innovations derived from them are the foundation of the civilized society in which we live today. All scientific endeavors begin with observations, or facts. However, the real goal of research activity is to convert accumulated knowledge to something with new technological, economic, or social value. Innovation is an essential aspect to assure the continued survival of humanity. And often, as my half-century of research reflects, the act of turning facts into values is facilitated by dialogue. Thus, to acquire the necessary combined wisdom, scientists must have ongoing conversations with the societies they serve, as well as with their counterparts in other nations.

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Asymmetric Syntheses

Cited by 4 publications

References 154 publications

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Fakten sind der Feind der Wahrheit – Betrachtungen über Zufallsentdeckungen und ungeahnte Entwicklungen der asymmetrischen Katalyse

Facts are the Enemy of Truth—Reflections on Serendipitous Discovery and Unforeseen Developments in Asymmetric Catalysis

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