Application of hydroxyproline derivatives in enantioselective α-amination reactions in organic and aqueous environments a structure-activity relationship study /
We examined the activity of a series of L-hydroxyproline derivatives in enantioselective alpha-amination reaction between diethyl azodicarboxylate and propanal both in organic and aqueous media. In organic media most of the catalysts showed high activity and enantioselectivities comparable to that a...
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Main Authors: | |
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Format: | Article |
Published: |
2017
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Series: | STRUCTURAL CHEMISTRY
28 No. 2 |
Subjects: | |
doi: | 10.1007/s11224-016-0873-z |
mtmt: | 30452962 |
Online Access: | http://publicatio.bibl.u-szeged.hu/27953 |
Summary: | We examined the activity of a series of L-hydroxyproline derivatives in enantioselective alpha-amination reaction between diethyl azodicarboxylate and propanal both in organic and aqueous media. In organic media most of the catalysts showed high activity and enantioselectivities comparable to that accessible with L-proline that is among the best catalysts in the reaction. The catalysts showed good activity under aqueous conditions as well; however, only low enantioselectivities were obtained in this case, primarily due to the racemisation of the product under the reaction conditions. Thus, the attempted achiral acid/base additive-driven stereocontrol was not feasible on a practical level. |
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Physical Description: | 415-421 |
ISSN: | 1040-0400 |