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The first report of natural l-vasicine as tridentate chiral ligand for the enantioselective addition of diethylzinc to a variety of aliphatic and aromatic aldehydes is described. The ligand generates R-isomer of the secondary alcohols upto 98% ee. The quinazoline structure possibly imparts rigidity to the ligand and hence, consistently high enantioselectivity. The importance of the quinazoline ring was also supported by the reaction with other related ligands, partially lacking the structural features, thus resulting in poor enantioselectivity. 相似文献
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Mushtaq A. Aga Brijesh Kumar Abdul Rouf Bhahwal A. Shah Samar S. Andotra Subhash C. Taneja 《Helvetica chimica acta》2013,96(5):969-977
A facile and scalable methodology for the preparation of optically active (3S)‐1‐benzylpyrrolidin‐3‐ol ( 3 ), an important drug precursor, is reported. Starting from the naturally occurring alkaloid (?)‐vasicine ( 1 ), a major alkaloid of the plant Adhatoda vasica, 3 was obtained in 84% overall yield (Scheme 3). 相似文献
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