本次研究中，我們以氯雷他定（Loratadine）前驅物為基底延伸，成功合成出兩支1-氮二苯環庚烯酮衍生之亞磺醯胺手性化合物L1、L2，並將其分別作為4−二甲胺基吡啶 (DMAP) 型態催化劑應用於Steglich重排反應及不對稱酯化反應，以及作為Tsuji-Trost不對稱烯丙位烷化反應中的配體選擇。
L1、L2作為 DAMP 型態催化劑，很可惜在 Steglich 重排反應及不對稱酯化反應中，皆沒有催化功能，推測是結構中缺乏關鍵的 DMAP 結構及做為親核中心的氮受到本身立體障礙的影響，導致親和力下降，無法參與反應進行。
L1作為手性配體選擇，分別以丙二酸二第三丁酯及丙二腈作為親核試劑，在氬氣與 50 °C 下，以二(三甲基矽基)醯胺作為鹼，對 1, 3−二苯基丙烯及其衍生物進行 Tsuji-Trost 不對烯丙位烷化反應。在丙二酸二第三丁酯的例子中，以甲苯作為溶劑選擇，產率介於 10%−46%，最高達 46%，鏡像選擇性介於 9%−58%，最高達 58%；丙二腈的例子中，很可惜產率及鏡像選擇性都不高，其中以乙腈為溶劑選擇，有最高的產率 28%，然而沒有鏡像選擇性，推測乙腈溶劑取代手性配體與鈀金屬配位，進行背景反應而失去鏡像選擇性。

In our study, we use the precursor of Loratadine to synthesize two new compounds, L1 and L2, derived from 1-azastilbene and sulfinamide structure. The two compounds were applied as chiral catalysts of 4-dimethylaminopyridine (DMAP) type in Steglich rearrangement reaction and asymmetric esterification, and as chiral ligands in Trost asymmetric allylic alkylation (AAA) reaction.
Unfortunately, they did not have catalytic ability as chiral catalysts of DMAP type in neither Steglich rearrangement reaction nor asymmetric esterification. We supposed the structure of two compounds that they don’t contain the skeleton of DMAP, and also the nucleophilicity of both nitrogens were reduced by their steric hindrance.
L1 as the chiral ligands, using di-tert-butyl malonate and malononitrile as nucleophilic reagents, bis(trimethylsilyl)acetamide as base, 3-Diphenylpropene and its derivatives were carried out Tsuji-Trost asymmetric allylic alkylation (AAA) reaction under argon at 50 °C. In the case of di-tert-butyl malonate, using toluene as solvent, yields are between 10% to 46% with enantiomeric excesses of 9% to 58%. In the case of malononitrile, unfortunately, it didn’t lead good yields or enantiomeric excesses. We got the highest yield with 28%, but no chiral selectivity when using acetonitrile as solvent. We supposed acetonitrile would replace the coordination between L1 and Pd, and do the background−reaction.

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