Unnatural chiral N - Tert -butanesulfinyl α-amino acid synthesis; A general synthetic strategy to N -boc-phenylalanine analogue alternatives

摘要

This work provides a general approach to unnatural chiral N-tert-butanesulfinyl α-amino acid synthesis with high yields and excellent diastereoselectivities (dr up to 98:2). The asymmetric addition of organometallic reagents to N-tert-butylsulfinyl imino acetate proceeded with excellent diastereo- and regioselectivities even on a 10 mmol scale. The sterically constrained 2,6-dimethyltyrosine (Dmt) derivative was also readily prepared from commercially available and inexpensive starting materials through simple steps.