Journal
TETRAHEDRON-ASYMMETRY
Volume 20, Issue 16, Pages 1881-1891Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2009.07.006
Keywords
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Funding
- FP6 Programme [MEST-CT-2005-019780]
- COST D40 Programme on 'Innovative Catalysis'
- UK government (EPSRC) [EP/F033478/1]
- EPSRC [EP/F033478/1, EP/G026882/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/G026882/1, EP/F033478/1] Funding Source: researchfish
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A study of copper-phosphoramidite-catalysed ZnR2 and AlR3 additions to 1,1'-dicarbonyl-activated cyclic Michael acceptors has revealed high enantioselectivities for AlR3 (R = Me, Et) 1,4-addition to a range of 3-acylcoumarins (85-98% ee, trans:cis similar to 90:10) using commercial OF readily available ligands. Large substituents at the 6-position, and to some extent at the 5-position, of the coumarin are less well tolerated, nor is truncation of the coumarin motif to a comparable 2-acylcyclohexenone (ee values up to 78%). (C) 2009 Elsevier Ltd. All rights reserved.
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