Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 21st October 2020 from 07:00 AM to 07:00 PM (BST).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.

Issue 10, 2006
Previous Article Next Article

Enhanced stereocontrol in Diels–Alder reactions of chiral dienols

Author affiliations


This combined experimental–computational investigation demonstrates that the presence of a removable bromine substituent on a diene leads to complete π-diastereofacial and endo/exo stereoselection in both intermolecular and intramolecular Diels–Alder reactions. The influence of the bromine upon stereoselectivity is dramatic: the cycloaddition of nonbrominated precursor 18EEEEEE, for example, gives four diastereomeric products in a 55∶13∶16∶16 ratio; the bromine-containing analogue gives one stereoisomer within the limits of detection. The examination of B3LYP/6-31+G(d) transition structures allows an interpretation of these experimental findings. A method for the completely stereoselective synthesis of complimentary diastereomeric products (30ZZZZZZ and 31ZZZZ) from the same simple starting materials (28 and 2) is reported. Discrepancies between calculation and experiment in an earlier investigation into the Diels–Alder reaction are explained.

Graphical abstract: Enhanced stereocontrol in Diels–Alder reactions of chiral dienols

Back to tab navigation

Supplementary files

Article information

21 Feb 2006
14 Mar 2006
First published
18 Apr 2006

Org. Biomol. Chem., 2006,4, 2019-2024
Article type

Enhanced stereocontrol in Diels–Alder reactions of chiral dienols

T. N. Cayzer, N. A. Miller, M. N. Paddon-Row and M. S. Sherburn, Org. Biomol. Chem., 2006, 4, 2019
DOI: 10.1039/B602618D

Social activity

Search articles by author