Highly diastereo- and enantioselective synthesis of syn-b-substituted tryptophans via asymmetric Michael addition of a chiral equivalent of nucleophilic glycine and sulfonylindoles

Jiang Wang, Shengbin Zhou, Daizong Lin, Xiao Ding, Hualiang Jiang, Hong Liu

The asymmetric synthesis of syn-b-substituted tryptophan derivatives was carried out by the Michael addition of chiral equivalent of nucleophilic glycine with sulfonylindoles, and high diastereo- and enantioselectivities were achieved. The resulting adducts were readily converted to syn-b-substituted tryptophans in 96% yield, indicating that the proposed method is a highly efficient route to chiral syn-b-substituted tryptophans.