405304-72-5Relevant academic research and scientific papers
Regioselective and stereoselective nucleophilic ring opening reactions of a phenyl-substituted aziridine: Enantioselective synthesis of β-substituted tryptophan, cysteine, and serine derivatives
Xiong, Chiyi,Wang, Wei,Cai, Chaozhong,Hruby, Victor J.
, p. 1399 - 1402 (2002)
The asymmetric synthesis of β-phenyl-substituted cysteine, tryptophan, and serine derivatives was successfully developed. In this approach, the key intermediate, enantiomerically pure 3-phenylaziridine-2-carboxylic ester 7, was prepared from α,β-unsaturated ester 1 by employing the Sharpless asymmetric dihydroxylation. The aziridine 7 was treated with 4-methoxybenzylthiol, indole, and acetic acid to give β-phenyl-substituted cysteine, tryptophan, and serine, respectively, in a clean SN2 type ring opening at the C3 position. This general approach can be used to synthesize a variety of β-substituted novel amino acids.
