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Practical asymmetric synthesis of α-methylserine derivatives under mild phase-transfer conditions

✍ Scribed by Keiji Nakayama; Keiji Maruoka


Book ID
104095587
Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
181 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis


The enantioselective methylation reaction of phenyloxazoline tert-butyl ester 5 using (R)-4b as a catalyst under mild phase-transfer conditions provides optically active a-methylserine derivatives in moderate yields with high enantioselectivity. Other a-alkylated serine derivatives are also achievable in high yields with high enantioselectivity by using catalytic amount of (R)-4b.


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✍ Shigeru Arai; Makoto Oku; Toshimasa Ishida; Takayuki Shioiri 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 267 KB

The catalytic asymmetric alkylation reaction of 0t-fluorotetralones promoted by a chiral quaternary ammonium salt derived from cinchonine under phase-transfer catalyzed conditions was described. The reaction proceeded smoothly to give the desired products with up to 91% ee. This methodology provides