Novel stereoselective synthesis of functionalized oxazolidinones from chiral aziridines.
Enantiomerically pure N-(R)-alpha-methylbenzyl-4(R)-(chloromethyl)oxazolidinones (4R)-5a-k were synthesized in one step and high yields from various aziridine-2-methanols (S)-2a-k by intramolecular cyclization with phosgene. The alpha-methylbenzyl substituent on the nitrogen was easily cleaved to give both enanatiomers of 4-(chloromethyl)oxazolidinones (R)-7a and (S)-7a. (R)-7a was used for the efficient syntheses of (L)-homophenylalaninol analogues (S)-12a-j. We also applied the same methodology to prepare oxazolidinones 9a-c containing a heteroatom-substituted alkyl group at C-4 in high yields.
Park
Chan Sun
CS
Department of Chemistry, Sogang University, Seoul, Korea.
Kim
Min Sung
MS
Sim
Tae Bo
TB
Pyun
Do Kyu
DK
Lee
Cheol Hae
CH
Choi
Daeock
D
Lee
Won Koo
WK
Chang
Jae-Won
JW
Ha
Hyun-Joon
HJ