301674-58-8Relevant academic research and scientific papers
Reaction of electron-deficient N-sulfinylanilines with chiral α-hydroxy acids: A new process for the synthesis of enantiomerically pure α-hydroxy amides
Chidambaram,Zhu,Penmetsa,Kronenthal,Kant
, p. 6017 - 6020 (2000)
A practical procedure to prepare enantiomerically pure α-hydroxy amides from chiral α-hydroxy acids and electron-deficient anilines via N-sulfinylaniline derivatives has been developed. (C) 2000 Elsevier Science Ltd.
A practical synthesis of the RARγ agonist, BMS-270394
Chidambaram, Ramakrishnan,Kant, Joydeep,Zhu, Jason,Lajeunesse, Jean,Sirard, Pierre,Ermann, Peter,Schierling, Peter,Lee, Peter,Kronenthal, David
, p. 632 - 636 (2002)
A novel synthesis of 1 (BMS-270394), a nuclear retinoic acid receptor (RARγ) agonist, is reported. The synthesis includes an enantioselective reduction of α-ketoacid 4 to the corresponding chiral α-hydroxy acid 7 using a NaBH4/L-tartaric acid mixture and a novel coupling between 7 and an electron-deficient aniline 11 which was activated via N-sulfinyl derivative 15 to form chiral α-hydroxy amide 16. The synthesis was completed by a racemization-free hydrolysis of 16 to the corresponding α-hydroxy amidoacid 1 using KOSiMe3 in acetonitrile.
