Tags

Type your tag names separated by a space and hit enter

Synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed asymmetric allylic substitution.
J Org Chem. 2003 Aug 08; 68(16):6197-201.JO

Abstract

The asymmetric synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed allylic substitution was described. The Ir-catalyzed allylic substitution of diphenylimino glycinate with allylic phosphates proceeded smoothly even at 0 degrees C and gave branch products with high enantioselectivity (up to 97% ee), when chiral bidentate phosphite bearing the 2-ethylthioethyl group was employed. In addition, both diastereomers of the branch products were synthesized stereoselectively by simply switching the base employed. These methods were also applied to the asymmetric synthesis of quaternary alpha-amino acids.

Authors+Show Affiliations

Kanayama T
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Yoshida K
No affiliation info available
Miyabe H
No affiliation info available
Kimachi T
No affiliation info available
Takemoto Y
No affiliation info available

MeSH

AlkylationAllyl CompoundsAmino AcidsCatalysisIridiumMolecular ConformationPhosphitesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

12895050

Citation

Kanayama, Takatoshi, et al. "Synthesis of Beta-substituted Alpha-amino Acids With Use of Iridium-catalyzed Asymmetric Allylic Substitution." The Journal of Organic Chemistry, vol. 68, no. 16, 2003, pp. 6197-201.
Kanayama T, Yoshida K, Miyabe H, et al. Synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed asymmetric allylic substitution. J Org Chem. 2003;68(16):6197-201.
Kanayama, T., Yoshida, K., Miyabe, H., Kimachi, T., & Takemoto, Y. (2003). Synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed asymmetric allylic substitution. The Journal of Organic Chemistry, 68(16), 6197-201.
Kanayama T, et al. Synthesis of Beta-substituted Alpha-amino Acids With Use of Iridium-catalyzed Asymmetric Allylic Substitution. J Org Chem. 2003 Aug 8;68(16):6197-201. PubMed PMID: 12895050.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed asymmetric allylic substitution. AU - Kanayama,Takatoshi, AU - Yoshida,Kazumasa, AU - Miyabe,Hideto, AU - Kimachi,Tetsutaro, AU - Takemoto,Yoshiji, PY - 2003/8/5/pubmed PY - 2004/2/28/medline PY - 2003/8/5/entrez SP - 6197 EP - 201 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 16 N2 - The asymmetric synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed allylic substitution was described. The Ir-catalyzed allylic substitution of diphenylimino glycinate with allylic phosphates proceeded smoothly even at 0 degrees C and gave branch products with high enantioselectivity (up to 97% ee), when chiral bidentate phosphite bearing the 2-ethylthioethyl group was employed. In addition, both diastereomers of the branch products were synthesized stereoselectively by simply switching the base employed. These methods were also applied to the asymmetric synthesis of quaternary alpha-amino acids. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12895050/Synthesis_of_beta_substituted_alpha_amino_acids_with_use_of_iridium_catalyzed_asymmetric_allylic_substitution_ DB - PRIME DP - Unbound Medicine ER -