Tags

Type your tag names separated by a space and hit enter

Iridium-catalyzed asymmetric double allylic alkylation of azlactone: efficient access to chiral α-amino acid derivatives.
Chem Commun (Camb). 2022 Mar 03; 58(19):3142-3145.CC

Abstract

An unprecedented Ir-catalyzed enantioselective double allylic alkylation of less bulky cyclic imine glycinate (azlactone) was rationally designed and developed, providing various bisallylated chiral amino acid derivatives. Control experiments revealed that this transformation proceeds in a sequential manner featuring quasi-dynamic kinetic resolution of the initially-formed monoallylation intermediates.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Cheng X
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072, P. R. China. cjwang@whu.edu.cn. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, 230021, China.
Shen C
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072, P. R. China. cjwang@whu.edu.cn. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, 230021, China.
Dong XQ
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072, P. R. China. cjwang@whu.edu.cn. Suzhou Institute of Wuhan University, Suzhou, Jiangsu, 215123, P. R. China.
Wang CJ
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072, P. R. China. cjwang@whu.edu.cn. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, 230021, China.

MeSH

AlkylationAllyl CompoundsAmino AcidsCatalysisIridiumLactonesMolecular StructureStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

35174829

Citation

Cheng, Xiang, et al. "Iridium-catalyzed Asymmetric Double Allylic Alkylation of Azlactone: Efficient Access to Chiral Α-amino Acid Derivatives." Chemical Communications (Cambridge, England), vol. 58, no. 19, 2022, pp. 3142-3145.
Cheng X, Shen C, Dong XQ, et al. Iridium-catalyzed asymmetric double allylic alkylation of azlactone: efficient access to chiral α-amino acid derivatives. Chem Commun (Camb). 2022;58(19):3142-3145.
Cheng, X., Shen, C., Dong, X. Q., & Wang, C. J. (2022). Iridium-catalyzed asymmetric double allylic alkylation of azlactone: efficient access to chiral α-amino acid derivatives. Chemical Communications (Cambridge, England), 58(19), 3142-3145. https://doi.org/10.1039/d2cc00328g
Cheng X, et al. Iridium-catalyzed Asymmetric Double Allylic Alkylation of Azlactone: Efficient Access to Chiral Α-amino Acid Derivatives. Chem Commun (Camb). 2022 Mar 3;58(19):3142-3145. PubMed PMID: 35174829.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iridium-catalyzed asymmetric double allylic alkylation of azlactone: efficient access to chiral α-amino acid derivatives. AU - Cheng,Xiang, AU - Shen,Chong, AU - Dong,Xiu-Qin, AU - Wang,Chun-Jiang, Y1 - 2022/03/03/ PY - 2022/2/18/pubmed PY - 2022/3/11/medline PY - 2022/2/17/entrez SP - 3142 EP - 3145 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 58 IS - 19 N2 - An unprecedented Ir-catalyzed enantioselective double allylic alkylation of less bulky cyclic imine glycinate (azlactone) was rationally designed and developed, providing various bisallylated chiral amino acid derivatives. Control experiments revealed that this transformation proceeds in a sequential manner featuring quasi-dynamic kinetic resolution of the initially-formed monoallylation intermediates. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/35174829/Iridium_catalyzed_asymmetric_double_allylic_alkylation_of_azlactone:_efficient_access_to_chiral_α_amino_acid_derivatives_ DB - PRIME DP - Unbound Medicine ER -