Diisopropyloxy(η2-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes

Frédéric Cadoret; Pascal Retailleau; Yvan Six

doi:10.1016/j.tetlet.2006.08.117

Diisopropyloxy(η²-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes

Frédéric Cadoret
, Pascal Retailleau
, Yvan Six

Institut de Chimie des Substances Naturelles

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

Abstract

The reaction of 3 equiv of cyclopentylmagnesium chloride with 2 equiv of titanium(IV) isopropoxide at low temperature (-70 to -50 °C) leads to the formation of 1 equiv of diisopropyloxy(η²-cyclopentene)titanium containing low amounts of the starting Grignard reagent. The sequential addition of two electrophiles onto this titanium complex involved as an intermediate in Kulinkovich-type reactions delivers various 1,2-disubstituted cyclopentane rings with generally high diastereoselectivity. Mechanistic considerations and possible extensions of this method are discussed.

Original language	English
Pages (from-to)	7749-7753
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2006.08.117
Publication status	Published - 30 Oct 2006
Externally published	Yes

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10.1016/j.tetlet.2006.08.117

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title = "Diisopropyloxy(η2-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes",

abstract = "The reaction of 3 equiv of cyclopentylmagnesium chloride with 2 equiv of titanium(IV) isopropoxide at low temperature (-70 to -50 °C) leads to the formation of 1 equiv of diisopropyloxy(η2-cyclopentene)titanium containing low amounts of the starting Grignard reagent. The sequential addition of two electrophiles onto this titanium complex involved as an intermediate in Kulinkovich-type reactions delivers various 1,2-disubstituted cyclopentane rings with generally high diastereoselectivity. Mechanistic considerations and possible extensions of this method are discussed.",

author = "Fr{\'e}d{\'e}ric Cadoret and Pascal Retailleau and Yvan Six",

year = "2006",

month = oct,

day = "30",

doi = "10.1016/j.tetlet.2006.08.117",

language = "English",

volume = "47",

pages = "7749--7753",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Diisopropyloxy(η2-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes

AU - Cadoret, Frédéric

AU - Retailleau, Pascal

AU - Six, Yvan

PY - 2006/10/30

Y1 - 2006/10/30

N2 - The reaction of 3 equiv of cyclopentylmagnesium chloride with 2 equiv of titanium(IV) isopropoxide at low temperature (-70 to -50 °C) leads to the formation of 1 equiv of diisopropyloxy(η2-cyclopentene)titanium containing low amounts of the starting Grignard reagent. The sequential addition of two electrophiles onto this titanium complex involved as an intermediate in Kulinkovich-type reactions delivers various 1,2-disubstituted cyclopentane rings with generally high diastereoselectivity. Mechanistic considerations and possible extensions of this method are discussed.

AB - The reaction of 3 equiv of cyclopentylmagnesium chloride with 2 equiv of titanium(IV) isopropoxide at low temperature (-70 to -50 °C) leads to the formation of 1 equiv of diisopropyloxy(η2-cyclopentene)titanium containing low amounts of the starting Grignard reagent. The sequential addition of two electrophiles onto this titanium complex involved as an intermediate in Kulinkovich-type reactions delivers various 1,2-disubstituted cyclopentane rings with generally high diastereoselectivity. Mechanistic considerations and possible extensions of this method are discussed.

U2 - 10.1016/j.tetlet.2006.08.117

DO - 10.1016/j.tetlet.2006.08.117

M3 - Article

AN - SCOPUS:33748977462

SN - 0040-4039

VL - 47

SP - 7749

EP - 7753

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Diisopropyloxy(η2-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes

Abstract

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Diisopropyloxy(η²-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes