TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

Luigi Anastasia; Elios Giannini; Giuseppe Zanoni; Giovanni Vidari

doi:10.1016/j.tetlet.2005.06.149

TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

Luigi Anastasia, Elios Giannini, Giuseppe Zanoni, Giovanni Vidari

IRCCS Policlinico San Donato

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

Abstract

TiF₄ has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state.

Original language	English
Pages (from-to)	5803-5806
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2005.06.149
Publication status	Published - Aug 29 2005

Keywords

Aldehydes
Allylsilane
Biomimetic reactions
Cyclization
TiF

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/j.tetlet.2005.06.149

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title = "TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes",

abstract = "TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state.",

keywords = "Aldehydes, Allylsilane, Biomimetic reactions, Cyclization, TiF",

author = "Luigi Anastasia and Elios Giannini and Giuseppe Zanoni and Giovanni Vidari",

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T1 - TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

AU - Anastasia, Luigi

AU - Giannini, Elios

AU - Zanoni, Giuseppe

AU - Vidari, Giovanni

PY - 2005/8/29

Y1 - 2005/8/29

N2 - TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state.

AB - TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state.

KW - Aldehydes

KW - Allylsilane

KW - Biomimetic reactions

KW - Cyclization

KW - TiF

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M3 - Article

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EP - 5806

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 35

ER -

TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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