Synthesis of C-2-symmetrical chiral diamines: diastereoselective addition to bis(1,3-oxazolidinyl)alkanes with Grignard reagents

Authors
Yamauchi, T Higashiyama, K Kubo, H Ohmiya, S
Citation
T. Yamauchi et al., Synthesis of C-2-symmetrical chiral diamines: diastereoselective addition to bis(1,3-oxazolidinyl)alkanes with Grignard reagents, TETRAHEDR-A, 11(14), 2000, pp. 3003-3015
Citations number
76
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
14
Year of publication
2000
Pages
3003 - 3015
Database
ISI
SICI code
0957-4166(20000728)11:14<3003:SOCCDD>2.0.ZU;2-S
Abstract
Asymmetric syntheses of C-2-symmetrical chiral 1,4- and 1,5-diamines with s tereogenic centers adjacent to the nitrogen atom have been accomplished. Ch iral diamines were prepared by diastereoselective alkylations of bisoxazoli dine, which was derived from (R)-phenylglycinol. Methyl and phenyl Grignard reagents were employed as alkylating reagents. In addition, tertiary chira l diamines were readily converted to primary diamines in high yield. (C) 20 00 Elsevier Science Ltd. All rights reserved.