Diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide

Authors
van der Sluis, M Dalmolen, J de Lange, B Kaptein, B Kellogg, RM Broxterman, QB
Citation
M. Van Der Sluis et al., Diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide, ORG LETT, 3(24), 2001, pp. 3943-3946
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
24
Year of publication
2001
Pages
3943 - 3946
Database
ISI
SICI code
1523-7060(20011129)3:24<3943:DAOABT>2.0.ZU;2-N
Abstract
[GRAPHICS] The highly diastereoselective addition of allylzinc bromide to imines deriv ed from (R)-phenylglycine amide is reported. Homoallylamines with high enan tiomeric purity are obtained from the adducts in three steps on removal of the chiral auxiliary by means of a nonreductive protocol. Removal of the au xiliary by hydrogenation leads to the saturated amines, also in high enanti omeric purity.