摘要
碳碳双键不对称环氧化反应得到的手性环氧化物是一类重要手性单元,是合成许多手性药物和天然产物的重要中间体,也是有机合成中的重要手性合成子。通过手性催化剂催化烯烃的不对称环氧化是获得手性环氧化合物的重要途径,但是,均相催化剂的分离与循环使用问题制约了该方法的发展与应用,而将均相催化剂固载则是解决问题的有效途径。
本论文围绕不对称环氧化催化剂的固载开展了以下三方面的研究工作。
1.多聚亮氨酸在介孔分子筛MCM-41上的固载及其在不对称环氧化反应中的应用。
多聚亮氨酸作为一类无毒、稳定性好、反应条件温和的非金属不对称环氧化催化剂应用于α,β-不饱和酮的不对称环氧化。在本课题组前期工作的基础上,我们分别采用了三种不同方法对多聚亮氨酸用介孔分子筛MCM-41进行固载,得到三种固载催化剂,并考察了在查尔酮不对称环氧化反应中的催化性能,主要结果如下:
(1) 通过吸附方式,使用介孔分子筛MCM-41固载正丁胺引发聚合的聚亮氨酸得到了MCM-41吸附固载聚亮氨酸催化剂。
(2) 通过共价键将(EtO)_3Si(CH_2)_3NH_2(APTES)枝接于分子筛MCM-41,获得官能化的分子筛MCM-AP,然后利用MCM-AP引发亮氨酸NCA聚合,获得了MCM-41枝接固载聚亮氨酸催化剂MCM-AP-PLL。
(3) 利用APTES先引发亮氨酸NCA聚合,再通过聚合物末端的(EtO)_3Si-以共价键方式将聚合物枝接固载于分子筛MCM-41,得到另一种MCM-41枝接固载聚亮氨酸催化剂AP-PLL-MCM。
This dissertation includes three parts.1. Immobilization of poly(L-leucine) on mesoporous molecular sieve MCM-41 and asymmetric epoxidation of α,β-unsaturated ketones with the immobilized poly(L-leucine) catalysts.Poly(L-leucine)s were immobilized onto mesoporous molecular sieve MCM-41 through physical absorption or covalently bonding. (1) Poly(L-leucine)s with various chain lengths were prepared by the n-BuNH_2 initiated polymerization of N-carboxyanhydrides of L-leuine (LeuNCA) in THF and immobilized on the MCM-41 by absorption. (2) Amino-functionalized mesoporous molecular sieve (MCM-AP) was prepared by reaction of (3-aminopropropyl)triethoxysilane (APTES) with MCM-41. Utilizing the MCM-AP as initiator, LeuNCA was polymerized in THF at room temperature for 72 h under a nitrogen atmosphere to provide the MCM-41-immobilized poly(L-leucine) catalyst, MCM-AP-PLL, with different degrees of polymerization (n). (3) Utilizing APTES as initiator, LeuNCA was polymerized in THF and subsequently covalently grafted on MCM-41 to obtain another catalyst AP-PLL-MCM. These catalysts were characterized by FT-IR, elemental analysis, 13C CP/MAS NMR, TG-SDTA and XRD.The Julia'-Colonna asymmetric epoxidation of benzalacetophenone was used as the model reaction to evaluate the performance of the immobilized poly(L-leucine). Under optimal condition, these immobilized catalysts, especially the covalently grafted ones, showed excellent catalytic activities and enantioselectivities. At average chain length n = 30, the MCM-AP-PLL catalyst exhibited the highest activity and enantioselectivity (up to 96.5%ee with 89.7% yield). The AP-PLL-MCM catalyst with n = 40 gave desired epoxide with 92.1%ee and 90% yield. MCM-adsorbed catalyst with n = 45 displayed 88.3%ee and 93.2% yield in the epoxidation under otherwise
identical conditions. The effect of chain length is significant on catalytic activity and enantioselectivity, showing that it is necessary to use poly(L-leucine) with n ≥ 30 to achieve good results. The MCM41-grafted Poly(L-leucine) catalysts could be very easily separated from the reaction mixture by filtration, which made recycling of catalyst very simple. The recovered MCM-AP-PLL catalyst retained catalytic properties at least for six runs (92%ee).2. Silica-grafted Poly(L-leucine) catalysts and their application in the asymmetric epoxidation of α,β-unsaturated ketones.Base on previous works of our group, we improved the immobilization method solving the problems of repeatability in preparing the immobilized catalysts and decrease of enantioselectivity in catalyst recycling. The silica-grafted AP-PLL-Silica gel was prepared similar to the MCM-41 analog. Using APTES as initiator, LeuNCA was polymerized in THF and then bound to silica gel via the covalent Si-O bond, which was characterized by FT-IR, elemental analysis, and ~(13)C CP/MAS.With poly(L-leucine) n = 30, this grafted catalyst showed excellent enantioselectivity (97.0%ee with 92.4% yield) in the model reaction of epoxidation of benzalacetophenone, significantly higher than the 87.3%ee of unsupported polyamino acid, 79.2%ee of silica-adsorbed catalysts and 92%ee of APTES, respectively. The effects of chain length of poly(L-leucine) on catalytic activity and enantioselectivity were also investigated. The average chain length affected both catalytic activity and enantioselectivity significantly. When chain length greater than 30 (n ≥ 30) is necessary to achieve acceptable enantioselectivity.The recycling and reuse of AP-PLL-Silica gel catalysts were further investigated. The catalyst was easy to recover and had a very low loss rate of about 2% per recycle. It is noteworthy that recycling did not decrease the catalytic performance of immobilized catalyst. After six times of recycling the enantioselectivity of the epoxidation of benzalacetophenone is still up to 95%ee.
3. Exploration of synthesis and immobilization chiral iminium salts catalyst.(1) A racemic binaphthyl-based chiral iminium with grafting groups was designed and synthesized through seven steps.(3) Two kinds of
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