Method of Inducing Chirality to Epoxides Using 2,3:4,6 di-O-isopropylidene-2-keto-L-gulonic Acid Monohydrate
    1.
    发明申请
    Method of Inducing Chirality to Epoxides Using 2,3:4,6 di-O-isopropylidene-2-keto-L-gulonic Acid Monohydrate 有权
    使用2,3:4,6二-O-异亚丙基-2-酮-L-古洛糖酸一水合物诱导环氧化物手性的方法

    公开(公告)号:US20100136635A1

    公开(公告)日:2010-06-03

    申请号:US12626843

    申请日:2009-11-27

    CPC classification number: C12P17/02

    Abstract: The present invention relates to a recyclable method to prepare chirally pure epoxides directly from olefins using a novel chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate as chiral inducer and anhydrous hydrogen peroxide in the form of urea hydrogen peroxide adduct (UHP) as oxidant and lipase enzyme as catalyst. Under the influence of lipase, the chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate is converted to per-acid in situ by the oxidant urea hydrogen peroxide which in turn transfers oxygen to olefin inducing chirality to the product epoxide. Using this technique, important epoxide building blocks of different industrially important compounds can be prepared with good yield and moderate enantioselectivity. Chiral epoxidation of olefins with environment friendly catalytic system that can be recycled is highly desirable in the context of Green Chemistry for preparation of many industrially important compounds.

    Abstract translation: 本发明涉及使用新型手性酸2,3,4,6-二-O-异亚丙基-2-酮-L-古洛糖酸一水合物作为手性诱导剂和无水氢气从烯烃直接制备手性纯环氧化物的可循环方法 过氧化脲以尿素过氧化氢加合物(UHP)为氧化剂,脂肪酶为催化剂。 在脂肪酶的影响下,手性酸2,3:4,6-二-O-异亚丙基-2-酮-L-古洛糖酸一水合物通过氧化剂尿素过氧化氢原位转化为过酸, 氧气到烯烃诱导产物环氧化物的手性。 使用这种技术,可以以良好的产率和适度的对映选择性制备重要的不同工业重要化合物的环氧化物结构单元。 在环境友好的催化体系下可以循环使用的烯烃的手性环氧化在绿色化学方面是非常需要的,用于制备许多工业上重要的化合物。

    Method of inducing chirality to epoxides using 2,3:4,6 di-O-isopropylidene-2-keto-L-gulonic acid monohydrate
    2.
    发明授权
    Method of inducing chirality to epoxides using 2,3:4,6 di-O-isopropylidene-2-keto-L-gulonic acid monohydrate 有权
    使用2,3:4,6二-O-异亚丙基-2-酮-L-古洛糖酸一水合物对环氧化物诱导手性的方法

    公开(公告)号:US08148118B2

    公开(公告)日:2012-04-03

    申请号:US12626843

    申请日:2009-11-27

    CPC classification number: C12P17/02

    Abstract: The present invention relates to a recyclable method to prepare chirally pure epoxides directly from olefins using a novel chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate as chiral inducer and anhydrous hydrogen peroxide in the form of urea hydrogen peroxide adduct (UHP) as oxidant and lipase enzyme as catalyst. Under the influence of lipase, the chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate is converted to per-acid in situ by the oxidant urea hydrogen peroxide which in turn transfers oxygen to olefin inducing chirality to the product epoxide. Using this technique, important epoxide building blocks of different industrially important compounds can be prepared with good yield and moderate enantioselectivity. Chiral epoxidation of olefins with environment friendly catalytic system that can be recycled is highly desirable in the context of Green Chemistry for preparation of many industrially important compounds.

    Abstract translation: 本发明涉及使用新型手性酸2,3,4,6-二-O-异亚丙基-2-酮-L-古洛糖酸一水合物作为手性诱导剂和无水氢气从烯烃直接制备手性纯环氧化物的可循环方法 过氧化脲以尿素过氧化氢加合物(UHP)为氧化剂,脂肪酶为催化剂。 在脂肪酶的影响下,手性酸2,3:4,6-二-O-异亚丙基-2-酮-L-古洛糖酸一水合物通过氧化剂尿素过氧化氢原位转化为过酸, 氧气到烯烃诱导产物环氧化物的手性。 使用这种技术,可以以良好的产率和适度的对映选择性制备重要的不同工业重要化合物的环氧化物结构单元。 在环境友好的催化体系下可以循环使用的烯烃的手性环氧化在绿色化学方面是非常需要的,用于制备许多工业上重要的化合物。

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