手性相转移催化剂设计及应用和三氟甲基酮不对称Aldol反应
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摘要
手性相转移催化作用作为不对称催化领域的重要组成部分,可实现多种不对称转化。本论文从设计和合成新型手性相转移催化剂的角度出发,以光学纯的联二萘酚为起始原料,合成了一系列新型的链状双螺环季铵盐。
我们以醛与2-卤代-N,N-二苯基乙酰胺的不对称Darzens反应为模板反应,研究了链状双螺环季铵盐的催化活性和选择性。以中等到当量的收率和中等到较高的对映选择性合成了一系列反式为主的手性α,β-环氧乙酰胺衍生物,反顺比最高可达13.4:1,反式产物的ee值最高可达74%。
α-氨基膦酸作为α-氨基酸的含磷类似物,具有多种生物活性。通过C–C键的形成反应,构建手性α-氨基膦酸及其衍生物的例子并不多见。我们首次成功实现了二苯酮亚胺甲基膦酸酯与α,β-不饱和酮的不对称Michael加成反应。在新型手性链状双螺环季铵盐作用下,以最高77%的对映选择性得到手性α-氨基膦酸衍生物。
潜手性三氟甲基砌块的催化不对称转化是合成手性含三氟甲基化合物的重要策略之一。我们以二甲基锌和手性氨基醇配体为催化剂,首次成功实现了三氟甲基酮和重氮酸酯的不对称Aldol反应,反应的最高对映选择性可达72%。
In recent years, chiral phase-transfer catalysis (PTC) has been recognized as an important part in asymmetric synthesis due to its high activity in a series of asymmetric transformations. Herein we focused on the design and synthesis of new chiral phase-transfer catalysts and their applications in asymmetric reactions. These catalysts, bearing linker-structured N-spiroammonium units, were synthesized conveniently from commercially available optically pure 1,1’-bi-2-naphthol (BINOL) in moderate yields.
The activity and enantioselectivity of the phase-transfer catalysts was firstly evaluated in catalytic asymmetric Darzens reaction between aldehydes andα-haloamides. The desiredα,β-epoxy-amides were obtained in high yields (up to 99%) with moderate to good diastereo- and enantioselectivities (trans/cis up to 13.4/1, up to 74% ee (trans)).
As the analogues of the correspondingα-amino acids,α-aminophosphonic acids have diverse biological properties. However, there are rare successful examples of constructingα-aminophosphonic acids and their derivatives via C–C bond forming reactions. We first developed the Michael addition of the phosphoglycine ester toα,β-unsaturated ketones by the newly designed PTC, giving moderate to good enantioselectivities with up to 77% ee.
As we all know, it is a significant strategy to apply prochiral trifluoromethyl-containing building blocks in asymmetric transformations. We accomplished the aldol-type reaction of trifluoromethyl aryl ketones withα-diazoesters, with low to moderate enantioselectivities (up to 72% ee).
我们以醛与2-卤代-N,N-二苯基乙酰胺的不对称Darzens反应为模板反应,研究了链状双螺环季铵盐的催化活性和选择性。以中等到当量的收率和中等到较高的对映选择性合成了一系列反式为主的手性α,β-环氧乙酰胺衍生物,反顺比最高可达13.4:1,反式产物的ee值最高可达74%。
α-氨基膦酸作为α-氨基酸的含磷类似物,具有多种生物活性。通过C–C键的形成反应,构建手性α-氨基膦酸及其衍生物的例子并不多见。我们首次成功实现了二苯酮亚胺甲基膦酸酯与α,β-不饱和酮的不对称Michael加成反应。在新型手性链状双螺环季铵盐作用下,以最高77%的对映选择性得到手性α-氨基膦酸衍生物。
潜手性三氟甲基砌块的催化不对称转化是合成手性含三氟甲基化合物的重要策略之一。我们以二甲基锌和手性氨基醇配体为催化剂,首次成功实现了三氟甲基酮和重氮酸酯的不对称Aldol反应,反应的最高对映选择性可达72%。
In recent years, chiral phase-transfer catalysis (PTC) has been recognized as an important part in asymmetric synthesis due to its high activity in a series of asymmetric transformations. Herein we focused on the design and synthesis of new chiral phase-transfer catalysts and their applications in asymmetric reactions. These catalysts, bearing linker-structured N-spiroammonium units, were synthesized conveniently from commercially available optically pure 1,1’-bi-2-naphthol (BINOL) in moderate yields.
The activity and enantioselectivity of the phase-transfer catalysts was firstly evaluated in catalytic asymmetric Darzens reaction between aldehydes andα-haloamides. The desiredα,β-epoxy-amides were obtained in high yields (up to 99%) with moderate to good diastereo- and enantioselectivities (trans/cis up to 13.4/1, up to 74% ee (trans)).
As the analogues of the correspondingα-amino acids,α-aminophosphonic acids have diverse biological properties. However, there are rare successful examples of constructingα-aminophosphonic acids and their derivatives via C–C bond forming reactions. We first developed the Michael addition of the phosphoglycine ester toα,β-unsaturated ketones by the newly designed PTC, giving moderate to good enantioselectivities with up to 77% ee.
As we all know, it is a significant strategy to apply prochiral trifluoromethyl-containing building blocks in asymmetric transformations. We accomplished the aldol-type reaction of trifluoromethyl aryl ketones withα-diazoesters, with low to moderate enantioselectivities (up to 72% ee).
引文
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