Reductions of activated carbonyl compounds with chiral-bridged 1,4-dihydropyridines. An investigation of scope and structural effects

Talma, Auke; Jouin, Patrick; Vries, Johannes G. de; Troostwijk, Coos Bram; Buning, G. H. Werumeus; Waninge, Jan K.; Visscher, Johnny; Kellogg, Richard M.

doi:10.1021/ja00299a038

Cited by 92 publications

(35 citation statements)

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“…Single crystals suitable for X-ray analysis were obtained by vapour diffusion of pentane into a solution of (I) in MeOH/EtOAc (1: found: C 50.07, H 7.20, N 9.84%. Compound (II) was prepared from l,d-valine methyl ester hydrochloride according to the procedure described by Talma et al (1985) and was separated from the reaction mixture by crystallization from CH 2 Cl 2 ±light petroleum. )/3 (Á/') max < 0.001 Á& max = 0.36 e A Ê À3 Á& min = À0.34 e A Ê À3 H atoms were placed in calculated positions and restrained to ride on the atom to which they were bonded.…”

Section: Methodsmentioning

confidence: 99%

meso-N,N′-Oxalyldivaline

Perić¹,

Kojić‐Prodić²,

Makarević³

et al. 2001

Acta Crystallogr C

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The title compound, 2,2'-(oxalyldiimino)bis(3-methylbutanoic acid), C12H20N2O6, possesses a centre of symmetry. In the crystal, molecules are connected by hydrogen bonds between oxamide and carboxyl groups, similar to the pattern of the monoclinic forms of HO-Gly-CO-CO-Gly-OH and HO-Aib-CO-CO-Aib-OH (Gly is glycine and Aib is 2-aminoisobutyric acid). The characteristic torsion angles in the title compound are close to those in peptide alpha-helices.

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Section: Methodsmentioning

confidence: 99%

meso-N,N′-Oxalyldivaline

Perić¹,

Kojić‐Prodić²,

Makarević³

et al. 2001

Acta Crystallogr C

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“…A long-standing interest in NADH chemistry 15 and the desire to test the validity of some of the above ideas led us to try to prepare monomeric Zn II thiolate centres and to study their chemistry in order to understand better the role of the metal both in structural and catalytic capacity. 8 This interest in zinc thiolates (and sulfides) was stimulated concurrently by the intense activity in the chemistry of alkylzincs with carbonyl compounds, whereby zinc alkoxides play an essential role.…”

Section: Models For the Catalytically Active Zinc Of Hladhmentioning

confidence: 99%

(Nonracemic) thiols and Zn II . Structural and catalytic aspects of some natural and non-natural zinc thiolates

Kellogg¹,

Hof²

1996

J. Chem. Soc., Perkin Trans. 1

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The catalytically active Zn II ion of the enzyme horse liver alcohol dehydrogenase (HLADH) is well known to be coordinated to two thiolates and an imidazole. Attempts to prepare models of this catalytically active Zn II complex are complicated by the great tendency of Zn II thiolates to form oligomeric structures. Some approaches to monomeric structures are described. Work on this problem has led to spin-offs in the form of the use of β β-aminothiols as ligands in the addition of diethylzinc to aldehydes. Monomeric zinc complexes are believed to be the active intermediates in this reaction. Excellent control over the enantioselectivity can be obtained. Methods developed in recent years for the synthesis of a variety of functionalized chiral nonracemic thiols open the way to the development of a catalytic chemistry of thiols in general and Zn II thiolates in particular.

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“…This methodology using chloro-and iodocarboxylic acids as well as the bromo-acids has subsequently been widely studied, 820,821 including several kinetic studies. 35 47 In the presence of cesium carbonate, a "cesium effect" was advocated to explain the selectivity in the macrolactonization/oligomerization process 48 but was then ruled out by Galli and Mandolini,823 who demonstrated that there is no particular difference between cesium and other alkaline cations in this application.…”

Section: Macrolactonizations Through Alkylhalides Mesylates and Sulmentioning

confidence: 99%