A new diastereoselective approach to the synthesis of α-hydroxy- β-amino acids based on the frame of captodative olefins

Rafael Herrera; Hugo A. Jiménez-Vázquez; Joaquín Tamariz

A new diastereoselective approach to the synthesis of α-hydroxy- β-amino acids based on the frame of captodative olefins

Rafael Herrera, Hugo A. Jiménez-Vázquez, Joaquín Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

A new diasteroselective approach for the preparation of chiral α-hydroxy-β-amino acids is described. It is based on the conjugate addition of either (R)-(+)-methylbenzylamine (4) or its lithium salt to the captodative olefins: methyl 2-aroyloxy- and 2-methacryloxy acrylates, 1a-1b and 1c. The highest diastereoselectivity is obtained when the addition is carried out with the chiral lithium amide in the presence of trialkylsilyl chlorides.

Original language	English
Pages (from-to)	233-249
Number of pages	17
Journal	Arkivoc
Volume	2005
Issue number	6
State	Published - 20 Jun 2005

Keywords

(R)-(+)-methylbenzylamine
Captodative olefins
Conjugate addition
α-Hydroxy-β-amino acids

Cite this

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title = "A new diastereoselective approach to the synthesis of α-hydroxy- β-amino acids based on the frame of captodative olefins",

abstract = "A new diasteroselective approach for the preparation of chiral α-hydroxy-β-amino acids is described. It is based on the conjugate addition of either (R)-(+)-methylbenzylamine (4) or its lithium salt to the captodative olefins: methyl 2-aroyloxy- and 2-methacryloxy acrylates, 1a-1b and 1c. The highest diastereoselectivity is obtained when the addition is carried out with the chiral lithium amide in the presence of trialkylsilyl chlorides.",

keywords = "(R)-(+)-methylbenzylamine, Captodative olefins, Conjugate addition, α-Hydroxy-β-amino acids",

author = "Rafael Herrera and Jim{\'e}nez-V{\'a}zquez, {Hugo A.} and Joaqu{\'i}n Tamariz",

year = "2005",

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TY - JOUR

T1 - A new diastereoselective approach to the synthesis of α-hydroxy- β-amino acids based on the frame of captodative olefins

AU - Herrera, Rafael

AU - Jiménez-Vázquez, Hugo A.

AU - Tamariz, Joaquín

PY - 2005/6/20

Y1 - 2005/6/20

N2 - A new diasteroselective approach for the preparation of chiral α-hydroxy-β-amino acids is described. It is based on the conjugate addition of either (R)-(+)-methylbenzylamine (4) or its lithium salt to the captodative olefins: methyl 2-aroyloxy- and 2-methacryloxy acrylates, 1a-1b and 1c. The highest diastereoselectivity is obtained when the addition is carried out with the chiral lithium amide in the presence of trialkylsilyl chlorides.

AB - A new diasteroselective approach for the preparation of chiral α-hydroxy-β-amino acids is described. It is based on the conjugate addition of either (R)-(+)-methylbenzylamine (4) or its lithium salt to the captodative olefins: methyl 2-aroyloxy- and 2-methacryloxy acrylates, 1a-1b and 1c. The highest diastereoselectivity is obtained when the addition is carried out with the chiral lithium amide in the presence of trialkylsilyl chlorides.

KW - (R)-(+)-methylbenzylamine

KW - Captodative olefins

KW - Conjugate addition

KW - α-Hydroxy-β-amino acids

UR - http://www.scopus.com/inward/record.url?scp=23044477799&partnerID=8YFLogxK

M3 - Artículo

SN - 1424-6376

VL - 2005

SP - 233

EP - 249

JO - Arkivoc

JF - Arkivoc

IS - 6

ER -

A new diastereoselective approach to the synthesis of α-hydroxy- β-amino acids based on the frame of captodative olefins

Abstract

Keywords

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