ChemInform Abstract: Asymmetric Tandem Additions to Chiral Naphthyloxazolines. A New and Potent Chiral Auxiliary Resulting in a Major Improvement in Convenience and Efficiency

Excellent diastereofacial selectivities over a wide range of temperatures (−78 to 25 o C) were obtained with the title compounds with use of chiral oxazolines derived from (S)-valinol or (S)-tert-leucinol. These are the first useful levels of asymmetric induction observed without the presence of the chelating methoxyl groups. The dihydronaphthylcarbinols and aldehydes resulting from these additions were obtained in >98% ee