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Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars

Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars
Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars
The base-catalyzed Michael addition of primary nitro compounds derived from sugars with 2 equiv of methyl vinyl ketone or acrolein was followed, in situ, by an asymmetric intramolecular aldol cyclization, thus yielding 2-acyl-4-glyco-4-nitrocyclohexanol derivatives with high diastereoselectivity.
michael addition, aldol cyclization, nitro compounds, sugars, nitrocyclohexanols, derivatives
0040-4039
3673-3676
Berrocal, M.V.
5036aed0-e2e4-4172-a0b4-ca2a48be86bf
Gil, M.V.
3ba9dd82-e26f-43e2-a7ee-b8ce3361219a
Román, E.
9d18a1e4-53de-4a32-bee9-4451d1ae5995
Serrano, J.A.
777244b5-9b7b-423b-8520-eafd68064638
Hursthouse, M.B.
427032bc-428c-4396-adb0-b38e87e908e7
Light, M.E.
d04ad463-ba94-4c59-ab35-a64901f32501
Berrocal, M.V.
5036aed0-e2e4-4172-a0b4-ca2a48be86bf
Gil, M.V.
3ba9dd82-e26f-43e2-a7ee-b8ce3361219a
Román, E.
9d18a1e4-53de-4a32-bee9-4451d1ae5995
Serrano, J.A.
777244b5-9b7b-423b-8520-eafd68064638
Hursthouse, M.B.
427032bc-428c-4396-adb0-b38e87e908e7
Light, M.E.
d04ad463-ba94-4c59-ab35-a64901f32501

Berrocal, M.V., Gil, M.V., Román, E., Serrano, J.A., Hursthouse, M.B. and Light, M.E. (2005) Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars. Tetrahedron Letters, 46 (21), 3673-3676.

Record type: Article

Abstract

The base-catalyzed Michael addition of primary nitro compounds derived from sugars with 2 equiv of methyl vinyl ketone or acrolein was followed, in situ, by an asymmetric intramolecular aldol cyclization, thus yielding 2-acyl-4-glyco-4-nitrocyclohexanol derivatives with high diastereoselectivity.

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More information

Published date: 23 May 2005
Keywords: michael addition, aldol cyclization, nitro compounds, sugars, nitrocyclohexanols, derivatives

Identifiers

Local EPrints ID: 20724
URI: https://eprints.soton.ac.uk/id/eprint/20724
ISSN: 0040-4039
PURE UUID: ad11990f-6d82-4fac-96dc-789d0a9d145c

Catalogue record

Date deposited: 01 Mar 2006
Last modified: 22 Oct 2017 02:32

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Contributors

Author: M.V. Berrocal
Author: M.V. Gil
Author: E. Román
Author: J.A. Serrano
Author: M.B. Hursthouse
Author: M.E. Light

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