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- W2757457663 endingPage "17028" @default.
- W2757457663 startingPage "17022" @default.
- W2757457663 abstract "Direct catalytic C-C bond-forming addition to N-unprotected ketimines is an efficient and straightforward method of synthesizing N-unprotected tetrasubstituted amines that eliminates prior protection/deprotection steps and allows facile transformation of the products. Despite its advantages, however, N-unprotected ketimines have difficulties in C-C bond-forming reactions, and only a limited number of reactions and substrates are reported compared with their N-protected counterparts. Herein we report that N-unprotected trifluoromethyl ketimines are effective for C-C bond-forming reactions using Mannich-type reactions as a model case. We demonstrate that Lewis acid catalysis was effective for promoting reactions with various N-unprotected trifluoromethyl ketimines, and thiourea organocatalysis was effective for promoting highly enantioselective reactions with various carbonyl nucleophiles, providing direct access to various N-unprotected α- and/or β-tetrasubstituted amino acid esters. Furthermore, direct construction of vicinal tetrasubstituted chiral carbon stereocenters was achieved for the first time in a highly enantio- and diastereoselective manner. These results demonstrate the potential of N-unprotected ketimines as substrates applicable to many other addition reactions." @default.
- W2757457663 created "2017-10-06" @default.
- W2757457663 creator A5017628553 @default.
- W2757457663 creator A5024413605 @default.
- W2757457663 creator A5025752165 @default.
- W2757457663 creator A5034960043 @default.
- W2757457663 creator A5083893218 @default.
- W2757457663 date "2017-09-26" @default.
- W2757457663 modified "2023-10-14" @default.
- W2757457663 title "Direct Access to N-Unprotected α- and/or β-Tetrasubstituted Amino Acid Esters via Direct Catalytic Mannich-Type Reactions Using N-Unprotected Trifluoromethyl Ketimines" @default.
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