Silylcupration of acylimidazolides: A new synthesis of α-aminoacylsilanes and their synthetic applications

Bianca Flavia Bonini; Mauro Comes-Franchini; Mariafrancesca Fochi; Germana Mazzanti; Alfredo Ricci; Greta Varchi

doi:10.1016/S0277-5387(99)00401-5

Silylcupration of acylimidazolides: A new synthesis of α-aminoacylsilanes and their synthetic applications

Bianca Flavia Bonini, Mauro Comes-Franchini, Mariafrancesca Fochi, Germana Mazzanti, Alfredo Ricci, Greta Varchi

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6 Scopus citations

Abstract

Several new N-Boc-protected α-aminoacylsilanes from L-phenylalanine and L-isoleucine are synthesized via silylcupration of the corresponding imidazolides. The addition reaction of nucleophiles to the carbonyl moiety gives satisfactory yields of highly functionalized β-amino alcohols and statine analogues. The diastereoselectivity ranges from 30 to 98% and depends upon the nature of the C-nucleophile, on the structure of the starting amino acid as well as on the chelating properties of the Lewis acid employed. (C) 2000 Elsevier Science Ltd All rights reserved.

Original language	English (US)
Pages (from-to)	529-531
Number of pages	3
Journal	Polyhedron
Volume	19
Issue number	5
DOIs	https://doi.org/10.1016/S0277-5387(99)00401-5
State	Published - Mar 15 2000

Keywords

Lewis acid
Silylcupration
Statine analogues
α-Aminoacylsilanes
β-Amino alcohols

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0277-5387(99)00401-5

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title = "Silylcupration of acylimidazolides: A new synthesis of α-aminoacylsilanes and their synthetic applications",

abstract = "Several new N-Boc-protected α-aminoacylsilanes from L-phenylalanine and L-isoleucine are synthesized via silylcupration of the corresponding imidazolides. The addition reaction of nucleophiles to the carbonyl moiety gives satisfactory yields of highly functionalized β-amino alcohols and statine analogues. The diastereoselectivity ranges from 30 to 98% and depends upon the nature of the C-nucleophile, on the structure of the starting amino acid as well as on the chelating properties of the Lewis acid employed. (C) 2000 Elsevier Science Ltd All rights reserved.",

keywords = "Lewis acid, Silylcupration, Statine analogues, α-Aminoacylsilanes, β-Amino alcohols",

author = "Bonini, {Bianca Flavia} and Mauro Comes-Franchini and Mariafrancesca Fochi and Germana Mazzanti and Alfredo Ricci and Greta Varchi",

note = "Funding Information: This work was supported by the University of Bologna (Funds for Selected Research Topics, A.A. 1999-01) and by the National Project {\textquoteleft}Stereoselezione in Sintesi Organica. Metodologie ed Applicazioni{\textquoteright}. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.",

year = "2000",

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day = "15",

doi = "10.1016/S0277-5387(99)00401-5",

language = "English (US)",

volume = "19",

pages = "529--531",

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TY - JOUR

T1 - Silylcupration of acylimidazolides

T2 - A new synthesis of α-aminoacylsilanes and their synthetic applications

AU - Bonini, Bianca Flavia

AU - Comes-Franchini, Mauro

AU - Fochi, Mariafrancesca

AU - Mazzanti, Germana

AU - Ricci, Alfredo

AU - Varchi, Greta

N1 - Funding Information: This work was supported by the University of Bologna (Funds for Selected Research Topics, A.A. 1999-01) and by the National Project ‘Stereoselezione in Sintesi Organica. Metodologie ed Applicazioni’. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.

PY - 2000/3/15

Y1 - 2000/3/15

N2 - Several new N-Boc-protected α-aminoacylsilanes from L-phenylalanine and L-isoleucine are synthesized via silylcupration of the corresponding imidazolides. The addition reaction of nucleophiles to the carbonyl moiety gives satisfactory yields of highly functionalized β-amino alcohols and statine analogues. The diastereoselectivity ranges from 30 to 98% and depends upon the nature of the C-nucleophile, on the structure of the starting amino acid as well as on the chelating properties of the Lewis acid employed. (C) 2000 Elsevier Science Ltd All rights reserved.

AB - Several new N-Boc-protected α-aminoacylsilanes from L-phenylalanine and L-isoleucine are synthesized via silylcupration of the corresponding imidazolides. The addition reaction of nucleophiles to the carbonyl moiety gives satisfactory yields of highly functionalized β-amino alcohols and statine analogues. The diastereoselectivity ranges from 30 to 98% and depends upon the nature of the C-nucleophile, on the structure of the starting amino acid as well as on the chelating properties of the Lewis acid employed. (C) 2000 Elsevier Science Ltd All rights reserved.

KW - Lewis acid

KW - Silylcupration

KW - Statine analogues

KW - α-Aminoacylsilanes

KW - β-Amino alcohols

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UR - http://www.scopus.com/inward/citedby.url?scp=0034653153&partnerID=8YFLogxK

U2 - 10.1016/S0277-5387(99)00401-5

DO - 10.1016/S0277-5387(99)00401-5

M3 - Article

AN - SCOPUS:0034653153

VL - 19

SP - 529

EP - 531

JO - Polyhedron

JF - Polyhedron

SN - 0277-5387

IS - 5

ER -

Silylcupration of acylimidazolides: A new synthesis of α-aminoacylsilanes and their synthetic applications

Abstract

Keywords

ASJC Scopus subject areas

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