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Synlett 2015; 26(01): 67-72
DOI: 10.1055/s-0034-1379600
DOI: 10.1055/s-0034-1379600
cluster
Regio- and Diastereoselective Vinylogous Mannich Addition of 3-Alkenyl-2-oxindoles to α-Fluoroalkyl Aldimines
Weitere Informationen
Publikationsverlauf
Received: 24. September 2014
Accepted after revision: 03. November 2014
Publikationsdatum:
20. November 2014 (online)
Abstract
An efficient asymmetric vinylogous Mannich (AVM) addition reaction of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines has been developed. This reaction provided various optical active α-alkylidene-δ-amino-δ-fluoroalkyl oxindoles in excellent yields, complete γ-site regioselectivity, and excellent diastereoselectivities.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379600.
- Supporting Information
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- 15 General Procedure for the Synthesis of α-Alkylidene-δ-amino-δ-fluoroalkyl OxindolesA solution of KHMDS (0.36 mL, 1 M solution in THF) was slowly added to a dried Scheck flask containing 3-alkenyl-2-oxindoles 2 (0.36 mmol) in THF (2.0 mL) at –78 °C under N2 atmosphere. After stirring at –78 °C for 1 h, the mixture of 1 (0.3 mmol) and Ti(Oi-Pr)4 (0.33 mmol) in THF (1.0 mL) was added dropwise, and the mixture was stirred for 12 h at –78 °C. Then sat. aq NH4Cl solution and H2O was added at –78 °C. The mixture was brought to r.t. After 5 min, the mixture was filtered through Celite, and the filtrate was extracted with EtOAc. The combined organic solution was dried over MgSO4. After the removal of volatile solvents under vacuum, the crude product was purified by silica gel column chromatography to give the required product.
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