Stereoselective syn aldol reaction of the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of triethylborane

Gunda I. George; Eyüp Akgün

doi:10.1016/0040-4039(91)80073-F

Stereoselective syn aldol reaction of the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of triethylborane

Medicinal Chemistry

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Abstract

Aldol condensation of acetaldehyde and benzaldehyde with the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of one equivalent of triethylborane resulted in the formation of the corresponding 3-hydroxy-2-amino acid ester with excellent stereocontrol (>95% de ) for the formation of syn products. The stereochemical outcome of these reactions is rationalized via the selective formation of the (Z)-enolate of 1 in the presence of triethylborane.

Original language	English (US)
Pages (from-to)	5521-5524
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	40
DOIs	https://doi.org/10.1016/0040-4039(91)80073-F
State	Published - Sep 30 1991

Keywords

Aldol
Ester Enolate
Glycine
Syn Selectivity
Triethylborane

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10.1016/0040-4039(91)80073-F

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title = "Stereoselective syn aldol reaction of the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of triethylborane",

abstract = "Aldol condensation of acetaldehyde and benzaldehyde with the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of one equivalent of triethylborane resulted in the formation of the corresponding 3-hydroxy-2-amino acid ester with excellent stereocontrol (>95\% de ) for the formation of syn products. The stereochemical outcome of these reactions is rationalized via the selective formation of the (Z)-enolate of 1 in the presence of triethylborane.",

keywords = "Aldol, Ester Enolate, Glycine, Syn Selectivity, Triethylborane",

author = "George, \{Gunda I.\} and Ey{\"u}p Akg{\"u}n",

year = "1991",

month = sep,

day = "30",

doi = "10.1016/0040-4039(91)80073-F",

language = "English (US)",

volume = "32",

pages = "5521--5524",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Stereoselective syn aldol reaction of the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of triethylborane

AU - George, Gunda I.

AU - Akgün, Eyüp

PY - 1991/9/30

Y1 - 1991/9/30

N2 - Aldol condensation of acetaldehyde and benzaldehyde with the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of one equivalent of triethylborane resulted in the formation of the corresponding 3-hydroxy-2-amino acid ester with excellent stereocontrol (>95% de ) for the formation of syn products. The stereochemical outcome of these reactions is rationalized via the selective formation of the (Z)-enolate of 1 in the presence of triethylborane.

AB - Aldol condensation of acetaldehyde and benzaldehyde with the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of one equivalent of triethylborane resulted in the formation of the corresponding 3-hydroxy-2-amino acid ester with excellent stereocontrol (>95% de ) for the formation of syn products. The stereochemical outcome of these reactions is rationalized via the selective formation of the (Z)-enolate of 1 in the presence of triethylborane.

KW - Aldol

KW - Ester Enolate

KW - Glycine

KW - Syn Selectivity

KW - Triethylborane

UR - https://www.scopus.com/pages/publications/0026049456

UR - https://www.scopus.com/pages/publications/0026049456#tab=citedBy

U2 - 10.1016/0040-4039(91)80073-F

DO - 10.1016/0040-4039(91)80073-F

M3 - Article

AN - SCOPUS:0026049456

SN - 0040-4039

VL - 32

SP - 5521

EP - 5524

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

Stereoselective syn aldol reaction of the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of triethylborane

Abstract

Keywords

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