手性1-烷基-1,2-二磷杂环戊二烯与二苯基重氮甲烷的不对称1,3-偶极环加成反应。
Asymmetric 1,3-dipolar cycloaddition reaction of chiral 1-alkyl-1,2-diphospholes with diphenyldiazomethane.
作者信息
Ganushevich Yulia, Zagidullin Almaz, Kondrashova Svetlana, Latypov Shamil, Miluykov Vasili, Lönnecke Peter, Hey-Hawkins Evamarie
机构信息
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS 420088 Kazan Russia
Institute of Inorganic Chemistry, Leipzig University 04103 Leipzig Germany.
出版信息
RSC Adv. 2020 Oct 27;10(64):39060-39066. doi: 10.1039/d0ra08080b. eCollection 2020 Oct 21.
The 1,3-dipolar cycloaddition of chiral 1-alkyl-1,2-diphosphacyclopenta-2,4-dienes ((1-(-)-menthyl)oxymethyl-1,2-diphosphole and 1-(+)-neomenthyl-1,2-diphosphole) with diphenyldiazomethane leads to novel -chiral bicyclic phosphiranes having six chiral centers. The degree of diastereoselectivity depends on the substituent at phosphorus, and dramatically increases in the case of (+)-neomenthyl group (de up to 71%). DFT calculations indicate that the cycloaddition is thermodynamically controlled.
手性1-烷基-1,2-二磷杂环戊-2,4-二烯（（1-（-）-薄荷基）氧甲基-1,2-二磷杂环戊二烯和1-（+）-新薄荷基-1,2-二磷杂环戊二烯）与二苯基重氮甲烷的1,3-偶极环加成反应生成了具有六个手性中心的新型手性双环磷杂环丙烷。非对映选择性的程度取决于磷原子上的取代基，在（+）-新薄荷基取代的情况下显著增加（非对映体过量高达71%）。密度泛函理论计算表明，该环加成反应受热力学控制。
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