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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

Sang-sup Jew*, Byeong-Seon Jeong, Jeong-Hee Lee, Mi-Sook Yoo, Yeon-Ju Lee, Boon-saeng Park, Myoung Goo Kim and Hyeung-geun Park*

*Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Email: ssjewsnu.ac.kr , hgpksnu.ac.kr

S.-s. Jew, B.-S. Jeong, J.-H. Lee, M.-S. Yoo, Y.-J. Lee, B.-s. Park, M. G. Kim, H.-g. Park, J. Org. Chem., 2003, 68, 4514-4516.

DOI: 10.1021/jo034006t (free Supporting Information)


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Abstract

In systematic investigations to develop an efficient enantioselective synthetic method for α-alkyl-alanine by catalytic phase-transfer alkylation, the alkylation of 2-naphthyl aldimine tert-butyl ester in the presence of RbOH and O(9)-allyl-N-2',3',4'-trifluorobenzylhydrocinchonidinium bromide as catalyst at -35C showed the highest enantioselectivities.

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Key Words

O'Donnell Amino Acid Synthesis, α-amino acids, organocatalysis


ID: J42-Y2003