Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary

Kennosuke Itoh; Fumiya Odate; Takuma Karikomi; Keishi Obe; Tsutomu Miyamori; Hideaki Kamiya; Kenji Yoza; Kenichiro Nagai; Hideaki Fujii; Hiroyuki Suga; Ken Tokunaga

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Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary

机译：带有手性2-恶唑烷酮助剂的香豆素衍生物的新型不对称光二聚反应

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A novel asymmetric photodimerization reaction of coumarin derivatives bearing the ( S )-4-benzyl-2-oxazolidinone auxiliary provides only the syn -head-to-tail ( syn -HT) dimer with moderate diastereoselectivity (up to 75?:?25). The mechanism of complete syn -HT selectivity and moderate diastereoselectivity is proposed based on the result of density functional theory (DFT) calculation. The benzyl group of the ( S )-4-benzyl-2-oxazolidinone auxiliary in combination with a Lewis acid exerts effective diastereofacial shielding of the reaction site.

机译：带有（S）-4-苄基-2-恶唑烷酮助剂的香豆素衍生物的新型不对称光二聚反应仅提供具有中等非对映选择性的顺头对尾（syn -HT）二聚体（最高75？：？25）。。基于密度泛函理论（DFT）的计算结果，提出了完全顺式-HT选择性和中等非对映选择性的机理。（S）-4-苄基-2-恶唑烷酮辅助剂的苄基与路易斯酸的组合有效地对反应位点进行非对映体屏蔽。

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《RSC Advances》 |2019年第22期|共5页
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Kennosuke Itoh; Fumiya Odate; Takuma Karikomi; Keishi Obe; Tsutomu Miyamori; Hideaki Kamiya; Kenji Yoza; Kenichiro Nagai; Hideaki Fujii; Hiroyuki Suga; Ken Tokunaga;
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1. Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary [J] . Itoh Kennosuke, Odate Fumiya, Karikomi Takuma, RSC Advances . 2019,第22期

机译：CoMarin衍生物携带手性2-恶唑烷酮助剂的新型非对称光二维化反应
2. Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary [J] . Kennosuke Itoh, Fumiya Odate, Takuma Karikomi, RSC Advances . 2019,第22期

机译：带有手性2-恶唑烷酮助剂的香豆素衍生物的新型不对称光二聚反应
3. LEWIS ACID CATALYSIS IN INTERMOLECULAR [2+2] PHOTOCYCLOADDITION OF COUMARIN-3-CARBOXAMIDE BEARING 2-OXAZOLIDINONE AUXILIARY WITH n-PROPYL VINYL ETHER AND VINYL PIVALATE [J] . Itoh Kennosuke, Matsuura Junya, Kamiya Hideaki, Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 2018,第1期

机译：在分子间的路易斯酸催化[2 + 2]光电环加入香豆素-3-甲酰胺轴承2-恶唑烷酮助剂，用正丙基乙烯基醚和乙烯基挥舞
4. Regio- and Diastereoselective Photodimerization Reactions of Chiral Coumarin-3-Carboxamides [C] . Kennosuke Itoh, Fumiya Odate, Takuma Karikomi 日本化学会春季年会講演予稿集 . 2018

机译：手性香豆素-3-甲酰胺的测定和非对映选择性光电二聚体反应
5. Part I. Asymmetric synthesis of bicyclic analogues of risedronate as molecular probes of the mechanism of action of bisphosphonate antiosteoporotic drugs and potentially more efficacious antiosteoporotic agents. Part II. Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using the Bestmann ylide and their use in Wittig reactions. Part III. Asymmetric organocatalysis: 1. An investigation of alpha-hydroxylation of aldehydes; 2. Synthesis of a novel camphor-based alpha-aminotetrazole organocatalyst. [D] . Song, Xinyi. 2007

机译：第一部分：利塞膦酸盐双环类似物的不对称合成，作为双膦酸盐类抗骨质疏松药和潜在更有效的抗骨质疏松药作用机理的分子探针。第二部分使用Bestmann内酯从常见手性助剂轻松制备和官能化手性稳定化的叶基及其在Wittig反应中的用途。第三部分不对称有机催化：1.醛的α-羟基化研究； 2.合成新的基于樟脑的α-氨基四唑有机催化剂。
6. Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary [O] . Gianluca Martelli, Eleonora Marcucci, Mario Orena, 2009

机译：带有手性助剂的酰基氨基甲酸酯的随后的SN-SN反应引起的Aza-Baylis-Hillman加合物的对映体纯衍生物
7. Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary [O] . Kennosuke Itoh, Fumiya Odate, Takuma Karikomi, 2019

机译：CoMarin衍生物携带手性2-恶唑烷酮助剂的新型非对称光二维化反应

Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary

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