Memory of chirality in diastereoselective alpha-alkylation of isoleucine and allo-isoleucine derivatives.
[reaction: see text] alpha-Methylation of 3 gave 5 as a major product whereas 4 gave 6 predominantly, although both 3 and 4 have an (S)-chiral center at C(3). This indicates that chirality at C(2) in 3 and 4 was memorized in the corresponding intermediate 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.
Kawabata
T
T
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan. kawabata@scl.kyoyo-u.ac.jp
Chen
J
J
Suzuki
H
H
Nagae
Y
Y
Kinoshita
T
T
Chancharunee
S
S
Fuji
K
K
D000478:Alkylation; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D007532:Isoleucine / Q000031:analogs & derivatives* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D007202:Indicators and Reagents; D007532:Isoleucine