Synthesis of chiral primary 1-ferrocenylalkylamines via highly diastereoselective addition of organolithium compounds to ferrocenecarboxaldehyde imine derived from (S)-2-methoxy-1-phenylethylamine

Authors
Fukuda, T Takehara, A Haniu, N Iwao, M
Citation
T. Fukuda et al., Synthesis of chiral primary 1-ferrocenylalkylamines via highly diastereoselective addition of organolithium compounds to ferrocenecarboxaldehyde imine derived from (S)-2-methoxy-1-phenylethylamine, TETRAHEDR-A, 11(20), 2000, pp. 4083-4091
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
20
Year of publication
2000
Pages
4083 - 4091
Database
ISI
SICI code
0957-4166(20001020)11:20<4083:SOCP1V>2.0.ZU;2-C
Abstract
The imine 3 derived from ferrocenecarboxaldehyde 1 and (S)-2-methoxy-1-phen ylethylamine 2 was reacted with several organolithium compounds to give 1,2 -addition products 4 in good yields with excellent diastereoselectivities ( >98% de). The adducts 4 were readily converted to the corresponding primary 1-ferrocenylalkylamines 5 by hydrogenolysis or stereoretentive substitutio ns without racemization. (C) 2000 Elsevier Science Ltd. All rights reserved .