Highly Enantioselective Synthesis of α-Alkyl-alanines via the Catalytic Phase-Transfer Alkylation of 2-Naphthyl Aldimine tert-Butyl Ester by Using O(9)-Allyl-N(1)-2‘,3‘,4‘-trifluorobenzylhydrocinchonidinium Bromide

Highly Enantioselective Synthesis of α-Alkyl-alanines via the Catalytic Phase-Transfer Alkylation of 2-Naphthyl Aldimine tert-Butyl Ester by Using O(9)-Allyl-N(1)-2‘,3‘,4‘-trifluorobenzylhydrocinchonidinium Bromide

Systematic investigations to develop an efficient enantioselective synthetic method for α-alkyl-alanine by catalytic phase-transfer alkylation were performed. The alkylation of 2-naphthyl aldimine tert-butyl ester, 1E, with RbOH and O(9)-allyl-N-2‘,3‘,4‘-trifluorobenzylhydrocinchonidinium bromide, 6...

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Veröffentlicht in:Journal of organic chemistry 2003-05, Vol.68 (11), p.4514-4516
Hauptverfasser: Jew, Sang-sup, Jeong, Byeong-Seon, Lee, Jeong-Hee, Yoo, Mi-Sook, Lee, Yeon-Ju, Park, Boon-saeng, Kim, Myoung Goo, Park, Hyeung-geun
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung:Systematic investigations to develop an efficient enantioselective synthetic method for α-alkyl-alanine by catalytic phase-transfer alkylation were performed. The alkylation of 2-naphthyl aldimine tert-butyl ester, 1E, with RbOH and O(9)-allyl-N-2‘,3‘,4‘-trifluorobenzylhydrocinchonidinium bromide, 6, at −35 °C showed the highest enantioselectivities, up to 96% ee.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034006t