A new chiral oxazoline derived from camphor and its conversion to (R)-2-methylalkanoic acids

Chandrasekhar, Sosale and Amina, Kausar (2000) A new chiral oxazoline derived from camphor and its conversion to (R)-2-methylalkanoic acids. In: Tetrahedron: Asymmetry, 11 (11). pp. 2249-2253.

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Abstract

1S,5R,7R)-(-)-10, 10-Dimethyl-3-ethyl-4-oxa--atricyclo[5.2.1.0(1,5)]dec-2-ene 2 was prepared in 95% yield from (1S)-1-amino-2-exo-hydroxyapocamphane 1. The chiral oxazoline could be alkylated (Lhttp://eprints.iisc.ernet.in/cgi/users/home?screen=EPrint::Edit&eprintid=31175&stage=core#tDA/THF/-78 degrees 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.). (C) 2000 Elsevier Science Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	Tetrahedron: Asymmetry
Publisher:	Elsevier science
Additional Information:	Copyright of this article belongs to Elsevier science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	09 Aug 2010 05:27
Last Modified:	19 Sep 2010 06:13
URI:	http://eprints.iisc.ac.in/id/eprint/31175

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