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
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.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, M.E.
d04ad463-ba94-4c59-ab35-a64901f32501
23 May 2005
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.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
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), .
(doi:10.1016/j.tetlet.2005.03.162).
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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Published date: 23 May 2005
Keywords:
michael addition, aldol cyclization, nitro compounds, sugars, nitrocyclohexanols, derivatives
Identifiers
Local EPrints ID: 20724
URI: http://eprints.soton.ac.uk/id/eprint/20724
ISSN: 0040-4039
PURE UUID: ad11990f-6d82-4fac-96dc-789d0a9d145c
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Date deposited: 01 Mar 2006
Last modified: 15 Mar 2024 06:25
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Contributors
Author:
M.V. Berrocal
Author:
M.V. Gil
Author:
E. Román
Author:
J.A. Serrano
Author:
M.E. Light
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