A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control

Direct enantiocontrolled access to 1,3‐amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama‐aldol addition). The obtained δ‐hydroxyesters were redu...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-09, Vol.2007 (26), p.4293-4297
Main Authors: Broustal, Garance, Ariza, Xavier, Campagne, Jean-Marc, Garcia, Jordi, Georges, Yohan, Marinetti, Angela, Robiette, Raphaël
Format: Article
Language:English
Subjects:
1,5‐Diols
5-Diols
Aldol reactions
Allylation
Carbamates
Chemical Sciences
Organic chemistry
Palladium
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Summary:Direct enantiocontrolled access to 1,3‐amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama‐aldol addition). The obtained δ‐hydroxyesters were reduced to pent‐2‐ene‐1,5‐diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3‐asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six‐membered‐ring cyclic carbamates. Calculations enabled us to rationalize the observed stereoselectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700503