Reaction of C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 with the two Vilsmeier-Haack complexes POCl3·DMF and (CF3SO2)2O·DMF: An efficient one-step conversion to the corresponding formates R1-OCHO

Y. Cohen; V. Kotlyar; S. Koeller; J. P. Lellouche

doi:10.1055/s-2001-18395

Reaction of C2-symmetrical dialkoxysilanes R₁O-Si(R₂)₂-OR₁ with the two Vilsmeier-Haack complexes POCl₃·DMF and (CF₃SO₂)₂O·DMF: An efficient one-step conversion to the corresponding formates R₁-OCHO

Y. Cohen
, V. Kotlyar
, S. Koeller
, J. P. Lellouche

Department of Chemistry

Bar-Ilan University

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

6 Scopus citations

Abstract

The two electrophilic Vilsmeier-Haack complexes POCl₃·DMF 1 and (CF₃SO₂)₂O·DMF 2 react with C2-symmetrical dialkoxysilanes R₁O-Si(R₂)₂-OR₁ (R₁=(-)-menthyl or 3β-cholesteryl, R₂=Me, Ph or i-Pr: 5a-c/6a-c) affording the formates R₁-OCHO 7 and 8 in medium to good yields depending on conditions. The scope and limitations of this novel one-step deprotection of C2-symmetrical silaketals to formates are described.

Original language	English
Pages (from-to)	1543-1546
Number of pages	4
Journal	Synlett
Issue number	10
DOIs	https://doi.org/10.1055/s-2001-18395
State	Published - 2001

Keywords

Deprotection
Formates
Formylation
Protecting group inter-conversion
Vilsmeier-Haack complexes

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10.1055/s-2001-18395

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title = "Reaction of C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 with the two Vilsmeier-Haack complexes POCl3·DMF and (CF3SO2)2O·DMF: An efficient one-step conversion to the corresponding formates R1-OCHO",

abstract = "The two electrophilic Vilsmeier-Haack complexes POCl3·DMF 1 and (CF3SO2)2O·DMF 2 react with C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 (R1=(-)-menthyl or 3β-cholesteryl, R2=Me, Ph or i-Pr: 5a-c/6a-c) affording the formates R1-OCHO 7 and 8 in medium to good yields depending on conditions. The scope and limitations of this novel one-step deprotection of C2-symmetrical silaketals to formates are described.",

keywords = "Deprotection, Formates, Formylation, Protecting group inter-conversion, Vilsmeier-Haack complexes",

author = "Y. Cohen and V. Kotlyar and S. Koeller and Lellouche, \{J. P.\}",

year = "2001",

doi = "10.1055/s-2001-18395",

language = "אנגלית",

pages = "1543--1546",

journal = "Synlett",

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T1 - Reaction of C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 with the two Vilsmeier-Haack complexes POCl3·DMF and (CF3SO2)2O·DMF

T2 - An efficient one-step conversion to the corresponding formates R1-OCHO

AU - Cohen, Y.

AU - Kotlyar, V.

AU - Koeller, S.

AU - Lellouche, J. P.

PY - 2001

Y1 - 2001

N2 - The two electrophilic Vilsmeier-Haack complexes POCl3·DMF 1 and (CF3SO2)2O·DMF 2 react with C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 (R1=(-)-menthyl or 3β-cholesteryl, R2=Me, Ph or i-Pr: 5a-c/6a-c) affording the formates R1-OCHO 7 and 8 in medium to good yields depending on conditions. The scope and limitations of this novel one-step deprotection of C2-symmetrical silaketals to formates are described.

AB - The two electrophilic Vilsmeier-Haack complexes POCl3·DMF 1 and (CF3SO2)2O·DMF 2 react with C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 (R1=(-)-menthyl or 3β-cholesteryl, R2=Me, Ph or i-Pr: 5a-c/6a-c) affording the formates R1-OCHO 7 and 8 in medium to good yields depending on conditions. The scope and limitations of this novel one-step deprotection of C2-symmetrical silaketals to formates are described.

KW - Deprotection

KW - Formates

KW - Formylation

KW - Protecting group inter-conversion

KW - Vilsmeier-Haack complexes

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DO - 10.1055/s-2001-18395

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AN - SCOPUS:0034810153

SN - 0936-5214

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JF - Synlett

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Reaction of C2-symmetrical dialkoxysilanes R₁O-Si(R₂)₂-OR₁ with the two Vilsmeier-Haack complexes POCl₃·DMF and (CF₃SO₂)₂O·DMF: An efficient one-step conversion to the corresponding formates R₁-OCHO

Abstract

Keywords

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