1，4-二羰基-2-丁烯类化合物的不对称硫-Michael加成反应研究
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摘要
有机小分子催化以其反应条件温和、不含金属、低毒、原子经济、类似酶催化等特点,成为近年来备受关注且发展迅速的一种不对称合成方法。本文以手性双官能团硫脲生物碱为催化剂,研究了其催化叔丁硫醇和1,4-二羰基-2-丁烯类化合物(其中包括反式-4-氧代-4-芳基-2-丁烯酰胺类和反式-4-氧代-4-芳基-2-丁烯酮类化合物)的不对称硫-Michael加成反应的性能。合成了一系列α-硫代酰胺类和酮类手性化合物,并解决了该反应的高立体选择性和区域选择性(ee值最高可达97%)问题。
Organocatalysis have received great attention in asymmetric synthesis for its enzyme mimic, metal-free, atomatically economic and low toxic characters. In this thesis, the catalytic effects of the cinchona alkaloid-derived thiourea bifunctional catalysts as organocatalysts to asymmetric sulfa-Michael addition were investigated. The addition of tert-butyl mercaptan to 1, 4-dicarbonly but-2-enes including (E)-4-oxo-4-arylbutenamides and (E)-4-oxo-4-arylbutenones is developed to synthesize a series of chiral sulfur-substitutedα-stereogenic amides and ketones with high regioselectivity and enantioselectivity (ee values up to 97%).
Organocatalysis have received great attention in asymmetric synthesis for its enzyme mimic, metal-free, atomatically economic and low toxic characters. In this thesis, the catalytic effects of the cinchona alkaloid-derived thiourea bifunctional catalysts as organocatalysts to asymmetric sulfa-Michael addition were investigated. The addition of tert-butyl mercaptan to 1, 4-dicarbonly but-2-enes including (E)-4-oxo-4-arylbutenamides and (E)-4-oxo-4-arylbutenones is developed to synthesize a series of chiral sulfur-substitutedα-stereogenic amides and ketones with high regioselectivity and enantioselectivity (ee values up to 97%).
引文
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[42]详细信息见附录:2(2)
[43] CCDC817603 (11ad) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from TheCambridgeCrystallographic Data Centre via www. Ccdc.cam.ac.uk/data_request/cif.
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[42]详细信息见附录:2(2)
[43] CCDC817603 (11ad) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from TheCambridgeCrystallographic Data Centre via www. Ccdc.cam.ac.uk/data_request/cif.