An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation
作者:Byron K. Peters、Taigang Zhou、Janjira Rujirawanich、Alban Cadu、Thishana Singh、Wangchuk Rabten、Sutthichat Kerdphon、Pher G. Andersson
DOI:10.1021/ja5079877
日期:2014.11.26
sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation
使用铱催化的不对称氢化反应制备了几种手性磺酰基化合物。研究了乙烯基、烯丙基和高烯丙基砜的取代,无论烯烃相对于砜的位置如何,都保持了高对映选择性。二烷基取代获得了令人印象深刻的立体选择性,这通常是氢化中具有挑战性的底物。正如预期的那样,体积更大的 Z 底物比相应的 E 异构体氢化得更慢,并且对映选择性略低。
Catalytic Enantioselective Construction of Chiral γ-Azido Nitriles through Nitrile Group-Promoted Electrophilic Reaction of Alkenes
construction of enantioenriched γ-azido nitriles through the chiral sulfide-catalyzed asymmetric electrophilic thioazidation of allylic nitriles is disclosed. A wide range of electron-deficient and -rich aryl, heterocyclic aryl, and alkyl substituents are suitable on the substrates of allylic nitriles. The regio-, enantio-, and diastereoselectivities of the reactions are excellent. As versatile platform