An efficient synthesis of optically active eprozinol

Sakuraba, Shunji; Nakajima, N.; Achiwa, Kazuo

doi:10.1016/s0957-4166(00)80341-9

Cited by 18 publications

(1 citation statement)

References 4 publications

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“…[22]. Although this may not be seen as a shortfall today, derivatives (18) of BPPM have been developed, mainly through different nitrogen substituents, and derivatives such as PPPM (18c) still give d-amino acids [85,[87][88][89][90][91][92][93][94][95][96][97][98]. The ligands are also useful for the reduction of itaconic acid derivatives [3].…”

Section: Diop 749mentioning

confidence: 99%

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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Section: Diop 749mentioning

confidence: 99%

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Ager¹

2006

The Handbook of Homogeneous Hydrogenation

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Hydrogenation of Compounds ContainingCC,COandCNBonds

Wills

2009

Patai's Chemistry of Functional Groups

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Introduction Hydrogenation of C  C Bonds Hydrogenation of C  O Bonds Hydrogenation of C  N Bonds Conclusions

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Rhodium

and¹,

Carmona²

2006

The Handbook of Homogeneous Hydrogenation

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Monohydride (MH) catalysts, such as [RhH(CO)(PPh 3 ) 3 ], react with substrates such as alkenes, according to Scheme 1.1, yielding rhodium-alkyl intermediates which, by subsequent reaction with hydrogen, regenerate the initial monohydride catalyst. This mechanism is usually adopted by hydrogenation catalysts which contain an M-H bond. Dihydride Hydrogenation CatalystsMany of these catalysts are derived from metal complexes which, initially, do not contain metal hydride bonds, but can give rise to intermediate MH 2 (alkene) species. These species, after migratory insertion of the hydride to the coordinated alkene and subsequent hydrogenolysis of the metal alkyl species, yield the saturated alkane. At first glance there are two possibilities to reach MH 2 (alkene) intermediates which are related to the order of entry of the two reaction partners in the coordination sphere of the metal (Scheme 1.2).

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An efficient synthesis of optically active eprozinol

Cited by 18 publications

References 4 publications

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Hydrogenation of Compounds ContainingCC,COandCNBonds

Rhodium

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