A stereoselective approach to 1,3-amino alcohols protected as cyclic carbamates: Kinetic vs. thermodynamic control
(2007) European Journal of Organic Chemistry — n° 26, p. 4293-4297 (2007)
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- Abstract
- 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 delta-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
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Citations
Broustal, G., Ariza, X., Campagne, J.-M., Garcia, J., Georges, Y., Marinetti, A., & Robiette, R. (2007). A stereoselective approach to 1,3-amino alcohols protected as cyclic carbamates: Kinetic vs. thermodynamic control. European Journal of Organic Chemistry, 26, 4293-4297. https://doi.org/10.1002/ejoc.200700503 (Original work published 2007)