Memory of chirality in diastereoselective cr-alkylation of isoleucine and allo-isoleucine derivatives

Authors
Kawabata, T Chen, JY Suzuki, H Nagae, Y Kinoshita, T Chancharunee, S Fuji, K
Citation
T. Kawabata et al., Memory of chirality in diastereoselective cr-alkylation of isoleucine and allo-isoleucine derivatives, ORG LETT, 2(24), 2000, pp. 3883-3885
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
24
Year of publication
2000
Pages
3883 - 3885
Database
ISI
SICI code
1523-7060(20001130)2:24<3883:MOCIDC>2.0.ZU;2-6
Abstract
alpha -Methylation of 3 gave 5 as a major product whereas 4 gave 6 predomin antly, although both 3 and 4 have an (S)-chiral center at C(3). This indica tes that chirality at C(2) in 3 and 4 was memorized in the corresponding in termediate enolates and the induced chirality made a major contribution in the stereochemical course of the reaction, while chirality at the adjacent chiral center C(3) had little effect.