Preparation of Bicyclo[3.2.0]heptane-2-endo,7-endo-diols:  1,3-Diols with a Chiral Rigid Backbone

Preparation of Bicyclo[3.2.0]heptane-2-endo,7-endo-diols:  1,3-Diols with a Chiral Rigid Backbone

The easily available bicyclo[3.2.0]hept-3-en-6-ones (1a-f) have been converted into the corresponding bicyclo[3.2.0]heptane-2-endo,7-endo-diols (4a-f) in an efficient and stereoselective fashion. This preparation opens a route to a family of 1,3-diols with a chiral rigid backbone, potentially suitab...

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Veröffentlicht in:Journal of organic chemistry 2004-02, Vol.69 (4), p.1353-1356
Hauptverfasser: PERI, Francesca, BINASSI, Enrico, MANETTO, Antonio, MAROTTA, Emanuela, MAZZANTI, Andrea, RIGHI, Paolo, SCARDOVI, Noemi, ROSINI, Goffredo
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Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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container_end_page 1356
container_issue 4
container_start_page 1353
container_title Journal of organic chemistry
container_volume 69
creator PERI, Francesca
BINASSI, Enrico
MANETTO, Antonio
MAROTTA, Emanuela
MAZZANTI, Andrea
RIGHI, Paolo
SCARDOVI, Noemi
ROSINI, Goffredo
description The easily available bicyclo[3.2.0]hept-3-en-6-ones (1a-f) have been converted into the corresponding bicyclo[3.2.0]heptane-2-endo,7-endo-diols (4a-f) in an efficient and stereoselective fashion. This preparation opens a route to a family of 1,3-diols with a chiral rigid backbone, potentially suitable as nonracemic precursors for bidentate ligands in asymmetric synthesis.
doi_str_mv 10.1021/jo035324v
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subjects Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
title Preparation of Bicyclo[3.2.0]heptane-2-endo,7-endo-diols:  1,3-Diols with a Chiral Rigid Backbone
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