在本篇論文中,我們利用掌性苯乙胺及其衍生物來控制7-氯-2-庚烯甲酯進行分子內Michael 加成反應時之非鏡像立體選擇性,並且也研究(R)- α-苯乙胺加成至不同官能基之Michael acceptor 時,包括酯類、酮類和Weinreb 醯胺,其非鏡像立體選擇性的差異。最後,並將其應用來合成天然物(-)-allosedridine 和(-)-2'-epi-ethylnorlobelol。 In this thesis, we apply the chiral methylbenzylamine and their derivatives to control the diastereoselectivity of the methyl 7-chlorohept-2-enoate in intramolecular Michael addition reactions. And we also study the differences of the diastereoselectivity when (R)-α-ethylbenzylamine reacts with different Michael acceptors, including the ester, ketone and Weinreb amide. Finally, we apply this methodology to synthesize two natural products (-)-allosedridine and (-)-2'-epi-ethylnorlobelol.