本論文敘述以反式-4-三異丙基矽氧基-L-脯胺酸與樟腦磺醯胺衍生之掌性有機催化劑75b，催化α-矽氧基乙醛與N-對-甲苯磺醯基亞胺進行不對稱Mannich反應。進行一系列溶劑、添加劑，反應物之當量數對不對稱Mannich反應之影響，發現僅需5 mol %催化量以及6 mol % 4-硝基苯甲酸即可與N-對-甲苯磺醯基亞胺進行反應，得到87%產率與97%鏡像選擇性，若反應在異丙醇/二氯甲烷之混合溶劑中進行，可與不同取代基亞胺進行Mannich反應，最高可得到91%產率、99%鏡像選擇性以及85:15的非鏡像立體選擇性，而除了鄰位甲氧基取代之亞胺外，其餘皆可達到67–91%產率，非鏡像選擇性為85:15–52:48，syn產物可以得到90～＞99%的鏡像選擇性。

This thesis deals with the use of organocatalyst 75b, comprising of trans-4-TIPSO-L-proline and N-phenyl camphorsulfonamide skeletons, in the asymmetric Mannich reaction of α-silyloxyethanal to N-tosylimines, affording syn 1,2-amino alcohols with reasonable to good chemical yield (31% to 91%), slight to moderate diastereoselectivities (52:48 to 85:15) and moderate to good enatioselectivities (89 to >99% ee of the trans 89 products). An extensive and through screening on the solvents, additives and aldehyde equivalents identified that 5 mol % of the catalyst and 6 mol % of acid additive were able to efficiently provide 87% yield of the addition product with 97 % ee for the 4-methyl substituted example. Furthermore, it was found that the binary IPA-DCM solvent system was important for achieving good yields.

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