Remote Stereocontrol in the Synthesis of Acyclic 1,4-Diols and 1,4-Aminoalcohols from 2-Sulfinyl Dienes

详细信息    查看全文

• 作者：Roberto Fern谩ndez de la Pradilla ; Marina Velado ; Ignacio Colomer ; Carmen Simal ; Alma Viso ; Heinz Gornitzka ; Catherine Hemmert
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：October 3, 2014
• 年：2014
• 卷：16
• 期：19
• 页码：5200-5203
• 全文大小：300K
• ISSN：1523-7052

文摘

The highly diastereoselective conjugate addition of alcohols and amines (RXH) to enantiopure 2-sulfinyl dienes renders transient allylic sulfoxides which undergo sulfoxide鈥搒ulfenate rearrangement and sulfenate cleavage providing 2-ene-1,4-diols and 2-ene-1,4-aminoalcohols with up to 99:1 dr. The method allows for the generation of two stereocenters in a single synthetic operation with remote chirality transfer of one center into the other.