Application of sulfonyl chlorides and chiral amines in the efficient synthesis of nonracemic sulfinamides
作者： Karolina Kamińska , Elżbieta Wojaczyńska , Jacek Skarżewski , Andrzej Kochel , Jacek Wojaczyński
DOI: 10.1016/J.TETASY.2017.03.004
关键词:
摘要: Abstract A simple protocol that allows the preparation of separable epimeric sulfinamides from chiral amines and sulfonyl chlorides reduced in situ with triphenylphosphine presence KOH is described. Using this method, tosyl chloride nosyl were successfully reacted α-substituted primary to give five diastereomeric pairs, certain cases accompanied by a small amount corresponding sulfonamide. Enantiopure products isolated column chromatography. The obtained enantiomerically pure tested as organocatalysts asymmetric epoxide ring opening.
sci-hub.se 参考文章(26)
Yoshihiko Watanabe, Nobuyuki Mase, Moto-aki Tateyama, Takeshi Toru, An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine Tetrahedron-asymmetry. ,vol. 10, pp. 737- 745 ,(1999) , 10.1016/S0957-4166(99)00066-X
George M. Sheldrick, Crystal structure refinement with SHELXL Acta Crystallographica Section C-crystal Structure Communications. ,vol. 71, pp. 3- 8 ,(2015) , 10.1107/S2053229614024218
Xirui Lv, Qinjie Xiang, Qingle Zeng, Potassium Hydroxide-promoted SelectiveN-Monoalkylation of Chiralt-Butane- andp-Toluenesulfinamides Organic Preparations and Procedures International. ,vol. 46, pp. 164- 175 ,(2014) , 10.1080/00304948.2014.884373
Elizabeth M. Beck, Alan M. Hyde, Eric N. Jacobsen, Chiral sulfinamide/achiral sulfonic acid cocatalyzed enantioselective protonation of enol silanes. Organic Letters. ,vol. 13, pp. 4260- 4263 ,(2011) , 10.1021/OL201608A
Guangcheng Liu, Derek A. Cogan, Jonathan A. Ellman, Catalytic Asymmetric Synthesis of tert-Butanesulfinamide. Application to the Asymmetric Synthesis of Amines Journal of the American Chemical Society. ,vol. 119, pp. 9913- 9914 ,(1997) , 10.1021/JA972012Z
Elżbieta Wojaczyńska, Ilona Turowska-Tyrk, Jacek Skarżewski, Novel chiral bridged azepanes: stereoselective ring expansion of 2-azanorbornan- 3-yl methanols Tetrahedron. ,vol. 68, pp. 7848- 7854 ,(2012) , 10.1016/J.TET.2012.07.028
Mikael J. Södergren, Pher G. Andersson, New and highly enantioselective catalysts for the rearrangement of meso-epoxides into chiral allylic alcohols Journal of the American Chemical Society. ,vol. 120, pp. 10760- 10761 ,(1998) , 10.1021/JA982381A
Sang Eun Park, Eun Hye Nam, Hyeong Bin Jang, Joong Suk Oh, Surajit Some, Yong Seop Lee, Choong Eui Song, Enantioselective Alcoholysis of meso‐Glutaric Anhydrides Catalyzed by Cinchona‐Based Sulfonamide Catalysts Advanced Synthesis & Catalysis. ,vol. 352, pp. 2211- 2217 ,(2010) , 10.1002/ADSC.201000289
Irwin B. Douglass, Richard V. Norton, Superior method for preparing sulfinyl chlorides Journal of Organic Chemistry. ,vol. 33, pp. 2104- 2106 ,(1968) , 10.1021/JO01269A088
Peter Brandt, Christian Hedberg, Klaus Lawonn, Pedro Pinho, Pher G. Andersson, A Theoretical and Experimental Study of the Asymmetric Addition of Dialkylzinc toN-(Diphenylphosphinoyl)benzalimine Chemistry - A European Journal. ,vol. 5, pp. 1692- 1699 ,(1999) , 10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO;2-M