Addition of Lithium Anion of (Acetylmethylene)triphenylphosphorane to Nonracemic Sulfinimines: Total Synthesis of (+)-241D and Formal Total Synthesis of (+)-Preussin.,Organic Letters

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Addition of Lithium Anion of (Acetylmethylene)triphenylphosphorane to Nonracemic Sulfinimines: Total Synthesis of (+)-241D and Formal Total Synthesis of (+)-Preussin.
Organic Letters ( IF 4.9 ) Pub Date : 2020-08-27 , DOI: 10.1021/acs.orglett.0c02608
Sopan P Khandare ₁ , Polimera Obula Reddy ₁ , Kavirayani R Prasad ₁

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The addition of lithium anion of (acetylmethylene)triphenylphosphorane to nonracemic sulfinimines was investigated. It was found that the addition proceeded with good diastereoselectivity and further reaction of the formed sulfinimidophosphorane with several aldehydes afforded the β-sulfinamido substituted enones in good yields. The resultant enones were elaborated to the synthesis of alkaloid (+)-241D, to the formal total synthesis of (+)-preussin, and to the synthesis of aminocyclopentenol.

中文翻译：

将（乙酰基亚甲基）三苯基膦烷锂阴离子加到非外消旋的亚氨嘧啶上：（+）-241D的全合成和（+）-Preussin的形式的全合成。

研究了将（乙酰基亚甲基）三苯基膦烷的锂阴离子加到非外消旋亚氨基亚胺上。发现添加以良好的非对映选择性进行，并且所形成的亚磺酰亚胺基亚膦酰基膦与几种醛的进一步反应以良好的产率提供了β-亚磺酰胺基取代的烯酮。将得到的烯酮详细描述为生物碱（+）-241D的合成，（+）-普鲁酶的正式全合成以及氨基环戊烯醇的合成。

更新日期：2020-09-20

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