本實驗室先前開發出氮-亞柳胺基酸所衍生的掌性希夫鹼，進一步和硫酸氧釩化合物於氧氣飽和之甲醇溶劑中合成掌性的五價氧釩錯合物，在此我們發展出另一個系統是將氮-亞柳胺基酸取代成氮-亞柳胺基四氮唑，且將此類催化劑應用在催化不對稱醛醇加成反應。
在不對稱Mukaiyama 醛醇加成反應中，我們利用三甲基矽基烯酮縮醛和靛紅衍生物進行反應，分別選用氮-亞柳胺基酸所衍生的氧釩錯合物和氮-亞柳胺基四氮唑所衍生的氧釩錯合物作為催化劑，實驗結果發現兩類不同的催化劑所產生醛醇加成產物的絕對立體化學有互補的效果，其中以在柳醛模板 C-3(即R1) 為 第三丁基，C-5(即R2) 為溴基時，氮-亞柳胺基酸所衍生的氧釩錯合物具有最高的鏡像超越值 （93％ ee），而 R1為氫， R2為硝基時，氮-亞柳胺基四氮唑所衍生的氧釩錯合物可得到高產率及理想鏡像超越值（79％，-83％ ee），推測因為 R1和手性模板縮酸或四氮唑相互立體電子效應反轉，導致鍵結在赤道向的烯酮縮醛會從與R1同向或反向加成到由軸向配位到氧釩中心的靛紅，而得到互補的鏡像選擇性。

The asymmetric aldol reaction of isatin derivatives have been realized by using Pd(II)-BINAP complexes as catalysts from Mikami and co-workers. A series of chiral vanadyl complexes derived from N-salicylidene amino acids and tetrazoles were developed. Their structural idendities were proven by X-ray crystallographic analysis. It was found that they can achieve complementary asymmetric catalytic aldol processes in the addition of silyl ketene acetals (SKA) to isatins at -40oC in CH2Cl2 in 66-69h. The results indicate that complementary stereoelectronic bias imposed by the C3 substituent of the salicylidene template or the tetrazole moiety are responsible for the observed complementary enantiofacial preferences in the aldol addition. On the basis of the intrinsic coordination attributes around the vanadyl center of these chiral vanadyl(V) methoxide complexes, we would expect that the initially generated vanadyl-bound enolate should occupy the basal position trans to the Schiff base and the isatin substrate should take on the apical position trans to the V=O unit. Under such circumstance, si face of the carbonyl group of isatin would be blocked by the C-3 substituent (e.g., tert-butyl) of the salicylidene template. The best enantioselectivity (93% ee) can be achieved by using type-I catalyst bearing 3-tert-butyl and 5-bromo substituents. Complementary re-face blockage with high eneatioselectivity (up to -83% ee) can be effected by the tetrazole moiety by using type-II catalyst bearing only 5-nitro substituent.

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