Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction

Vergne, CarolineBouillon, Jean-PhilippeChastanet, JacquelineBois-Choussy, MicheleZhu, Jieping2010-11-252010-11-252010-11-25199810.1016/S0957-4166(98)00312-7https://infoscience.epfl.ch/handle/20.500.14299/58536Two short syntheses of D-N-Boc-3,5-bis(isopropyloxy)-4-methoxyphenylglycine, a central unit of vancomycin type antibiotics, have been developed. A diastereoselective Strecker amination reaction using (S)-phenylglycinol as a chiral inducer was the key step in the first synthesis, while Evans' electrophilic azidation technol. was employed for introducing both the amino function and the chirality in the second strategy. [on SciFinder (R)]Amination (Streckerdiastereoselective; asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); Asymmetric synthesis and induction (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); Substitution reaction (azidationEvans' electrophilic; asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies)glycine bisisopropyloxymethoxyphenyl asym synthesis; amination diastereoselective Strecker phenylglycinol chiral reagent; azidation electrophilic Evans one step chirality amino group addnAsymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reactiontext::journal::journal article::research article