Direct Substitution of Primary Allylic Amines with Sulfinate Salts
Xue-Song Wu, Yan Chen, Man-Bo Li, Meng-Guang Zhou and Shi-Kai Tian*
*Joint Laboratory of Green Synthetic Chemistry, Department of
Chemistry, University of Science and Technology of China, Hefei, Anhui 230026,
China, Email:
tiansk
ustc.edu.cn
X.-S. Wu, Y. Chen, M.-B. Li, M.-G. Zhou, S.-K. Tian, J. Am. Chem. Soc., 2012, 134, 14694-14697.
DOI: 10.1021/ja306407x
see article for more reactions
Abstract
In the presence of a Pd catalyst and excess boric acid, a range of α-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an α-selective fashion to give structurally diverse allylic sulfones in good to excellent yields with exclusive E selectivity. Use of BINOL as a ligand allowed the transformation of unsymmetric α-chiral primary allylic amines in good to excellent yields with excellent retention of ee.
see article for more examples
Key Words
ID: J48-Y2012-2900
