Open AccessGenerating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks
Author(s) -
Wei Wei,
Rama Kanwar Khangarot,
Lothar Stahl,
Cristina Veresmortean,
Padmanava Pradhan,
Yang Liu,
Barbara Zajc
Publication year - 2018
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.8b01358
Subject(s) - epimer , diastereomer , chemistry , sulfone , fluorine , carbon atom , asymmetric carbon , organic chemistry , stereochemistry , medicinal chemistry , optically active , ring (chemistry)
Diastereoselective fluorination of N-Boc ( R)- and ( S)-2,2-dimethyl-4-((arylsulfonyl)methyl)oxazolidines and a previously unknown diastereoselective epimerization at the fluorine-bearing carbon atom α to the sulfone was realized. Diastereoselectivities of both reactions were excellent for benzothiazolyl sulfones, allowing access to two enantiomerically pure diastereomers from one chiral precursor. To demonstrate synthetic utility, the benzothiazolyl sulfones were converted to diastereomerically pure ( S, S)- and ( R, S)-benzyl sulfones via sulfinate salts and to amino acids. To understand the diastereoselectivities, DFT analysis was performed.