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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

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journal contribution
posted on 2003-05-02, 00:00 authored by Sang-sup Jew, Byeong-Seon Jeong, Jeong-Hee Lee, Mi-Sook Yoo, Yeon-Ju Lee, Boon-saeng Park, Myoung Goo Kim, Hyeung-geun Park
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.

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