Asymmetric protonation of lithium enolates of alpha-amino acid derivatives with alpha-amino acid-based chiral Brønsted acids.
The reaction of lithium enolates of alpha-amino acid derivatives with chiral amides, easily synthesized from L-tert-leucine, gives corresponding optically active unnatural alpha-amino acid derivatives with up to 87% ee.
Futatsugi
Kentaro
K
Graduate School of Engineering, Nagoya University, SORST, Japan Science and Technology Corporation, Chikusa 464-8603, Japan.
Yanagisawa
Akira
A
Yamamoto
Hisashi
H
D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011522:Protons; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000577:Amides; D000596:Amino Acids; D004952:Esters; D009942:Organometallic Compounds; D011522:Protons; D008094:Lithium; D007930:Leucine