An Approach to the Stereoselective Synthesis of Enantiopure Dihydropyrroles and Aziridines from a Common Sulfinyl-Sulfinamide Intermediate

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• 作者：Alma Viso ; Roberto Fern谩ndez de la Pradilla ; Mercedes Ure帽a ; Robert H. Bates ; Miguel A. del 脕guila ; Ignacio Colomer
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：January 6, 2012
• 年：2012
• 卷：77
• 期：1
• 页码：525-542
• 全文大小：509K
• 年卷期：v.77,no.1(January 6, 2012)
• ISSN：1520-6904

文摘

The diastereoselective addition of lithiated vinyl sulfoxides to enantiopure sulfinimines provides direct access to a wide assortment of allylic sulfinamides in good yields and excellent selectivities. These adducts are key precursors to differently functionalized cis- and trans-dihydropyrroles. Modulation of the protecting group on nitrogen prior to cyclization has a significant impact on the stereochemical outcome, allowing for the selective preparation of 2,5-cis- or 2,5-trans-3-sulfinyl disubstituted dihydropyrroles from a common sulfinamide intermediate. Further research on halocyclization conditions has also yielded a stereoselective synthesis of trisubstituted vinyl aziridines from these chiral sulfinamides, simply by changing the halogenating agent.