Oxazoline as chiral auxiliary

The use of oxazolines as chiral auxiliaries for asymmetric Michael additions has yielded mixed results. For example, Langlois group reported modest dia-stereoselectivities (up to 60% de) for cyanide addition to a number of chiral... 

The use of oxazolines as chiral auxiliaries in the asymmetric syntheses of iso-quinoline alkaloids was investigated by Gawley and coworkers [56, 57]. Lithiation and substitution of 71 resulted in isoquinolines 72, which were obtained in high yields with ers of 90 10 to 97 3 (Scheme 20). The products 72 obtained by this route were enantiomeric with 70. The rationale is that the isopropyl group in the two different auxiliaries have the opposite orientation leading to different... 

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