New Chiral Catalysts ContainingN,O-Heterocycles Derived from Chiral Amino Alcohols
1999; Wiley; Volume: 1999; Issue: 12 Linguagem: Inglês
10.1002/(sici)1099-0690(199912)1999
ISSN1434-193X
AutoresOlga Juanes, Juan Carlos Rodrı́guez-Ubis, Ernesto Brunet, Helmut Pennemann, Michael Kossenjans, Jürgen Martens,
Tópico(s)Axial and Atropisomeric Chirality Synthesis
ResumoEuropean Journal of Organic ChemistryVolume 1999, Issue 12 p. 3323-3333 Full Paper New Chiral Catalysts Containing N,O-Heterocycles Derived from Chiral Amino Alcohols Olga Juanes, Olga Juanes Departamento de Química Orgánica. Facultad de Ciencias, C-I. Universidad Autónoma Madrid, E-28049-Madrid, Spain Fax: (internat) + 34-91/397-3966Search for more papers by this authorJuan Carlos Rodriguez-Ubis, Juan Carlos Rodriguez-Ubis Departamento de Química Orgánica. Facultad de Ciencias, C-I. Universidad Autónoma Madrid, E-28049-Madrid, Spain Fax: (internat) + 34-91/397-3966Search for more papers by this authorErnesto Brunet, Ernesto Brunet [email protected] Search for more papers by this authorHelmut Pennemann, Helmut Pennemann Universität Oldenburg, Fachbereich Chemie, D-26129 Oldenburg, Germany Fax: (internat.) + 49-441/798-3757Search for more papers by this authorMichael Kossenjans, Michael Kossenjans Universität Oldenburg, Fachbereich Chemie, D-26129 Oldenburg, Germany Fax: (internat.) + 49-441/798-3757Search for more papers by this authorJürgen Martens, Jürgen Martens [email protected] Universität Oldenburg, Fachbereich Chemie, D-26129 Oldenburg, Germany Fax: (internat.) + 49-441/798-3757Search for more papers by this author Olga Juanes, Olga Juanes Departamento de Química Orgánica. Facultad de Ciencias, C-I. Universidad Autónoma Madrid, E-28049-Madrid, Spain Fax: (internat) + 34-91/397-3966Search for more papers by this authorJuan Carlos Rodriguez-Ubis, Juan Carlos Rodriguez-Ubis Departamento de Química Orgánica. Facultad de Ciencias, C-I. Universidad Autónoma Madrid, E-28049-Madrid, Spain Fax: (internat) + 34-91/397-3966Search for more papers by this authorErnesto Brunet, Ernesto Brunet [email protected] Search for more papers by this authorHelmut Pennemann, Helmut Pennemann Universität Oldenburg, Fachbereich Chemie, D-26129 Oldenburg, Germany Fax: (internat.) + 49-441/798-3757Search for more papers by this authorMichael Kossenjans, Michael Kossenjans Universität Oldenburg, Fachbereich Chemie, D-26129 Oldenburg, Germany Fax: (internat.) + 49-441/798-3757Search for more papers by this authorJürgen Martens, Jürgen Martens [email protected] Universität Oldenburg, Fachbereich Chemie, D-26129 Oldenburg, Germany Fax: (internat.) + 49-441/798-3757Search for more papers by this author First published: 15 November 1999 https://doi.org/10.1002/(SICI)1099-0690(199912)1999:12 3.0.CO;2-WCitations: 8AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The enantioselectivity exerted by a new series of chiral catalysts containing N,O-heterocycles of different sizes has been checked in the addition of diethylzinc to benzaldehyde, which was used as a model reaction. The catalysts were derived from natural amino acids, following a relatively simple procedure, and in several cases excellent ee values were obtained. The results were complementary since ee's ranged from 98% (R) to 94% (S) excesses of the final 1-phenylpropan-1-ol. Molecular mechanics calculations suggested that the production of the R alcohol may be explained by a mechanism similar to that described by Noyori, in which ZnEt2 interacts solely with the N–C–C–OH fragment, whereas the formation of the S enantiomer needed the direct participation of the lateral chain of the parent amino acid and the N,O-heterocycle. References 1[1a] J. Martens, Top. Curr. 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