Novel stereoselective synthesis of functionalized oxazolidinones from chiral aziridines

被引：65

作者：

Park, CS

Kim, MS

Sim, TB

Pyun, DK

Lee, CH

Choi, D

Lee, WK ^{[1
]}

Chang, JW

Ha, HJ

机构：

[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea

[2] Hankuk Univ Foreign Studies, CheBioNex, Kyunggido 449791, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 01期

关键词：

D O I：

10.1021/jo025545l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：43 / 49

页数：7

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