Unknown

Dataset Information

0

Asymmetric synthesis of ?-allyl-?-aryl ?-amino acids by tandem alkylation/?-allylation of ?-iminoesters.

ABSTRACT: The first asymmetric synthesis of ?-allyl-?-aryl ?-amino acids by means of a three-component coupling of ?-iminoesters, Grignard reagents, and cinnamyl acetate is reported. Notably, the enolate from the tandem process provides a much higher level of reactivity and selectivity than the same enolate generated via direct deprotonation, presumably due to differences in the solvation/aggregation state. A novel method for removal of a homoallylic amine protecting group delivers the free amine congeners. The ?-allyl group offers a means to generate further valuable ?-amino acid structures as exemplified by ring closing metathesis to generate a higher ring homologue of ?-aryl-proline.

SUBMITTER: Curto JM 

PROVIDER: S-EPMC3983326 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.

Curto John M JM   Dickstein Joshua S JS   Berritt Simon S   Kozlowski Marisa C MC  

Organic letters 20140325 7

The first asymmetric synthesis of α-allyl-α-aryl α-amino acids by means of a three-component coupling of α-iminoesters, Grignard reagents, and cinnamyl acetate is reported. Notably, the enolate from the tandem process provides a much higher level of reactivity and selectivity than the same enolate generated via direct deprotonation, presumably due to differences in the solvation/aggregation state. A novel method for removal of a homoallylic amine protecting group delivers the free amine congener  ...[more]

Similar Datasets

Unknown Synthesis of quaternary ?-methyl ?-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine.
| S-EPMC3884032 | biostudies-literature
Unknown ?-Allyl-?-aryl ?-amino esters in the asymmetric synthesis of acyclic and cyclic amino acid derivatives by alkene metathesis.
| S-EPMC4059215 | biostudies-literature
Unknown Tandem Alkylation-Second-Order Asymmetric Transformation Protocol for the Preparation of Phenylalanine-Type Tailor-Made α-Amino Acids.
| S-EPMC6644829 | biostudies-literature
Unknown Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines.
| S-EPMC4506507 | biostudies-literature
Unknown Engineering acyclic stereocontrol in the alkylation of vinylglycine-derived dianions: asymmetric synthesis of higher alpha-vinyl amino acids.
| S-EPMC6054771 | biostudies-literature
Unknown Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.
| S-EPMC8133004 | biostudies-literature
Unknown Enantioselective catalytic synthesis of ?-aryl-?-SCF3-?2,2-amino acids.
| S-EPMC6989214 | biostudies-literature
Unknown ?-Vinylic Amino Acids: Occurrence, Asymmetric Synthesis and Biochemical Mechanisms.
| S-EPMC6029878 | biostudies-literature
Unknown Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.
| S-EPMC5651674 | biostudies-literature
Unknown Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans.
| S-EPMC3701415 | biostudies-literature