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首页> 外文OA文献 >Application of sulfonimidoyl substituted allyltitanium (IV) complexes to the asymmetric synthesis of alkenyloxiranes, 2,3-dihydrofurans, tetrahydrofurans, unsaturated proline analogues and allylic alcohols
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Application of sulfonimidoyl substituted allyltitanium (IV) complexes to the asymmetric synthesis of alkenyloxiranes, 2,3-dihydrofurans, tetrahydrofurans, unsaturated proline analogues and allylic alcohols

机译：磺酰亚胺基取代的烯丙基钛（IV）配合物在烯基环氧乙烷，2,3-二氢呋喃，四氢呋喃，不饱和脯氨酸类似物和烯丙基醇的不对称合成中的应用

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摘要

An asymmetric synthesis of 3-substituted unsaturated proline derivatives starting from the g,d-unsaturated a-amino acids is described in chapter 3. Amino acid derivatives were obtained through aminoalkylation of the sulfoximine substituted allyl (trisdiethylamino) titanium (IV) complexes with the N-tert-butylsulfonyl imino ester. Activation of sulfoximines through methylation, of the sulfoximine group follwed by Cl substitution, and subsequent DBU-mediated, intramolecular, nucleophilic substitution afforded the optically-pure proline derivatives in medium to high yields. An asymmetric synthesis of allylic alcohols from allylic sulfoximines and aldehydes is described in chapter 4. Lithiation and titanation of cyclic and acyclic allylic sulfoximines with ClTi(NEt2)3 and subsequent treatment with aldehydes gave, as described previously, enantio- and diastereomerically-pure, syn-configured, sulfoximine-substituted homoallylic alcohols. Treatment of these alcohols with n-BuCu resulted in a SN2¢ reaction, and delivered a enantio- and diastereomerically-pure allylic alcohols. An asymmetric synthesis of cycloalkenyl and alkenyloxiranes from allylic sulfoximines and aldehydes is described in chapter 1. Lithiation and titanation of cyclic and acyclic allylic sulfoximines with ClTi(NEt2)3 and subsequent treatment with aldehydes gave, as described previously, enantio- and diastereomerically pure, syn-configured, sulfoximine-substituted homoallylic alcohols with ClCO2CH(Cl)Me resulted in a facile substitution of the sulfoximine group by a Cl atom, with formation of the corresponding alkenyl chlorohydrins. In the case of the cycloalkenyl derivatives the substitution proceeded with high diastereoselectivities and retention of configuration, while in the case of the alkenyl derivatives, medium diastereoselectivities with invertion of configuration were observed. An asymmetric synthesis of 2,3-dihydrofurans and of unsaturated bicyclic tetrahydrofurans from allylic sulfoximines and aldehydes is described in chapter 2.
机译：第3章描述了从g，d-不饱和a-氨基酸开始的3取代不饱和脯氨酸衍生物的不对称合成。氨基酸衍生物是通过将亚砜亚胺取代的烯丙基（trisdiethylamino）钛（IV）配合物与氨基苯磺酸氨基烷基化而获得的。 N-叔丁基磺酰基亚氨基酯。通过甲基取代使亚砜亚胺基团被甲基取代活化，然后由DBU介导的分子内亲核取代，以中等至高收率提供了光学纯的脯氨酸衍生物。如第4章所述，由烯丙基亚砜基亚砜和醛类不对称合成烯丙醇。如前所述，用ClTi（NEt2）3对环状和无环烯丙基亚砜基亚甲基进行锂化和钛化，然后用醛进行处理，得到对映体和非对映体纯体，顺式配置的，亚磺酰亚胺取代的均烯丙基醇。用正丁基铜处理这些醇会导致SN2¢反应，并生成对映体和非对映体纯的烯丙基醇。如第1章所述，由烯丙基的亚砜基亚砜和醛类不对称合成环烯基和链烯基氧杂环丁烷。如前所述，用ClTi（NEt2）3对环和无环烯丙基亚砜基亚胺进行锂化和钛化，然后用醛进行处理，得到对映体和非对映体纯体，带有ClCO2CH（Cl）Me的顺式配置的亚磺酰亚胺取代的均烯丙基醇可轻松实现Cl原子取代亚磺酰亚胺基，并形成相应的烯基氯醇。在环烯基衍生物的情况下，取代以高非对映选择性和构型保留而进行，而在烯基衍生物的情况下，观察到中等非对映选择性且构型反转。第2章介绍了由烯丙基硫代亚砜和醛类不对称合成2,3-二氢呋喃和不饱和双环四氢呋喃的方法。

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    Gadamsetty Surendra Babu;

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  • 年度 2007
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  • 正文语种 eng
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