Evaluating β-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction

被引：69

作者：

Davies, Stephen G. ^{[1
]}

Russell, Angela J. ^{[1
]}

Sheppard, Ruth L. ^{[1
]}

Smith, Andrew D. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Organ Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 19期

关键词：

D O I：

10.1039/b711171a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

引用

页码：3190 / 3200

页数：11

共 72 条

[51] STEREOCHEMICAL STUDIES .32. ASYMMETRIC SYNTHESIS OF INTERMEDIATES FOR TOTAL SYNTHESIS OF STEROIDS AND TERPENES WITH L-PROLINE ENAMINE METHOD [J].

NAGASAWA, K ;

TAKAHASHI, H ;

HIROI, K ;

YAMADA, SI .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1975, 95 (01) :33-45

[52] Enamine-based organocatalysis with proline and diamines: The development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-Alder reactions [J].

Notz, W ;

Tanaka, F ;

Barbas, CF .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :580-591

[53] Safe and convenient procedure for solvent purification [J].

Pangborn, AB ;

Giardello, MA ;

Grubbs, RH ;

Rosen, RK ;

Timmers, FJ .

ORGANOMETALLICS, 1996, 15 (05) :1518-1520

[54] REAKTIONEN MIT MIKROORGANISMEN .1. DIE STEREOSPEZIFISCHE REDUKTION VON (+/-)-DELTA-4-9-METHYL-OCTALINDION-(3,8) [J].

PRELOG, V ;

ACKLIN, W .

HELVETICA CHIMICA ACTA, 1956, 39 (03) :748-757

[55] NONLINEAR EFFECTS IN ASYMMETRIC-SYNTHESIS - EXAMPLES IN ASYMMETRIC OXIDATIONS AND ALDOLIZATION REACTIONS [J].

PUCHOT, C ;

SAMUEL, O ;

DUNACH, E ;

ZHAO, S ;

AGAMI, C ;

KAGAN, HB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2353-2357

[56] Proline mediated asymmetric ketol cyclization: a template reaction [J].

Rajagopal, D ;

Moni, MS ;

Subramanian, S ;

Swaminathan, S .

TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1631-1634

[57] Density functional study of the proline-catalyzed direct aldol reaction [J].

Rankin, KN ;

Gauld, JW ;

Boyd, RJ .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (20) :5155-5159

[58] Asymmetric organocatalysis [J].

Seayad, J ;

List, B .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) :719-724

[59] Are Oxazolidinones really unproductive, parasitic species in proline catalysis? Thoughts and experiments pointing to an alternative view [J].

Seebach, Dieter ;

Beck, Albert K. ;

Badine, D. Michael ;

Limbach, Michael ;

Eschenmoser, Albert ;

Treasurywala, Adi M. ;

Hobi, Reinhard ;

Prikoszovich, Walter ;

Linder, Bernard .

HELVETICA CHIMICA ACTA, 2007, 90 (03) :425-471

[60] Inotropic activity of hydroindene amidinohydrazones [J].

Sevillano, LG ;

Melero, CP ;

Caballero, E ;

Tomé, F ;

Lelièvre, LG ;

Geering, K ;

Crambert, G ;

Carrón, R ;

Medarde, M ;

Feliciano, AS .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (01) :127-136

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