- A new chiral oxazoline derived from camphor and its conversion to (R)-2-methylalkanoic acids
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(1S,5R,7R)-(-)-10,10-Dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.01,5]dec-2-ene 2 was prepared in 95% yield from (1S)-1-amino-2-exo-hydroxyapocamphane 1. The chiral oxazoline could be alkylated (LDA/THF/-78°C/RX, RX=ethyl, n-propyl, n-butyl iodides or benzyl bromide) to 3 in 95% yield and >95% diastereoselectivity, and the products hydrolysed to (R)-2-methylalkanoic acids 4 (43-47% yield, 93-98% e.e.). Copyright (C) 2000 Elsevier Science Ltd.
- Chandrasekhar, Sosale,Kausar, Amina
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p. 2249 - 2253
(2007/10/03)
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