Looking for treasure in stereochemistry-land. A path marked by curiosity, obstinacy, and serendipity.

作者: Eusebio Juaristi

DOI: 10.1021/JO300195M

关键词:

摘要: Over the past 40 years, much of my research has evolved around various topics conformational analysis and asymmetric synthesis. This Perspective describes some salient contributions in eight different areas organic stereochemistry: (1) six-membered rings, (2) evaluation stereoelectronic interactions 1JC–H one-bond coupling constants (3) eclipsed conformation cis-2-tert-butyl-5-(tert-butylsulfonyl)-1,3-dioxane, (4) determination enthalpic entropic to ΔG°(CH2Ph) ΔG°(t-Bu), (5) study “attractive gauche effect” O–C–C–O segments, (6) examination salt effects on equilibria, (7) synthesis β-amino acids, (8) organocatalysis “Green” chemistry. It will be appreciated that a basic understanding principles physical chemistry been essential all projects. Furthermore, curiosity, enthusiasm, obstinacy, paying attention unexpected obse...

参考文章(172)
Modern aldol reactions Wiley-VCH Verlag GmbH. ,(2004) , 10.1002/9783527619566
NS Zefirov, LG Gurvich, AS Shashkov, MZ Krimer, EA Vorob'eva, None, Stereochemical studies—XX: Conformations of 1,2-trans-disubstituted cyclohexanes Tetrahedron. ,vol. 32, pp. 1211- 1219 ,(1976) , 10.1016/0040-4020(76)80074-9
Jerry A. Hirsch, Table of Conformational Energies—1967 Topics in Stereochemistry, Volume 1. pp. 199- 222 ,(2007) , 10.1002/9780470147108.CH4
Z. Tang, F. Jiang, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y.-D. Wu, Enantioselective direct aldol reactions catalyzed by L-prolinamide derivatives. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 101, pp. 5755- 5760 ,(2004) , 10.1073/PNAS.0307176101
Mustafa Tavasli, David O’Hagan, Christopher Pearson, Michael C. Petty, The fluorine gauche effect. Langmuir isotherms report the relative conformational stability of (+/-)-erythro- and (+/-)-threo-9,10-difluorostearic acids. Chemical Communications. pp. 1226- 1227 ,(2002) , 10.1039/B202891C
Guiliana Cardillo, Claudia Tomasini, Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids Chemical Society Reviews. ,vol. 25, pp. 117- 128 ,(1996) , 10.1039/CS9962500117
Dieter Seebach, Eusebio Juaristi, David D. Miller, Christof Schickli, Theodor Weber, Addition of chiral glycine, methionine, and vinylglycine enolate derivatives to aldehydes and ketones in the preparation of enantiomerically pure α-amino-β-hydroxy acids Helvetica Chimica Acta. ,vol. 70, pp. 237- 261 ,(1987) , 10.1002/HLCA.19870700129
Saul Wolfe, Gauche effect. Stereochemical consequences of adjacent electron pairs and polar bonds Accounts of Chemical Research. ,vol. 5, pp. 102- 111 ,(1972) , 10.1021/AR50051A003
Jun-An Ma, Recent Developments in the Catalytic Asymmetric Synthesis of α- and β-Amino Acids Angewandte Chemie International Edition. ,vol. 42, pp. 4290- 4299 ,(2003) , 10.1002/ANIE.200301600