First Highly Diastereoselective Synthesis of s yn α-Methyl β-Fluoroalkyl β-Amino Esters

First Highly Diastereoselective Synthesis of s yn α-Methyl β-Fluoroalkyl β-Amino Esters

A new two-step approach for the diastereoselective synthesis of the syn α-methyl β-fluoroalkyl β-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated β-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester e...

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Veröffentlicht in:Organic letters 1999-10, Vol.1 (7), p.977-980
Hauptverfasser: Fustero, Santos, Pina, Belén, García de la Torre, Marta, Navarro, Antonio, Ramírez de Arellano, Carmen, Simón, Antonio
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container_end_page 980
container_issue 7
container_start_page 977
container_title Organic letters
container_volume 1
creator Fustero, Santos
Pina, Belén
García de la Torre, Marta
Navarro, Antonio
Ramírez de Arellano, Carmen
Simón, Antonio
description A new two-step approach for the diastereoselective synthesis of the syn α-methyl β-fluoroalkyl β-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated β-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester enolates, with ZnI2/NaBH4 as the reducing agent. The process takes place with high syn diastereoselectivity and good to excellent yields. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction.
doi_str_mv 10.1021/ol990774o
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title First Highly Diastereoselective Synthesis of s yn α-Methyl β-Fluoroalkyl β-Amino Esters
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